| Date | Time | Type | Home School | Away School | Site |
| WED 4/1 | 4:30 PM | League | Southington | East Catholic | Southington High School - Tennis Courts |
| SAT 4/4 | 1:30 PM | League | Cheshire | Branford | Cheshire High School - Tennis Courts |
| SAT 4/4 | 10:00 AM | League | Cromwell | Old Saybrook | Cromwell Middle School - Waterous Park Tennis Courts |
| SAT 4/4 | 10:00 AM | League | East Hampton | Morgan | East Hampton High School - Tennis Courts |
| SAT 4/4 | 10:00 AM | League | Haddam Killingworth | Valley Regional | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| SAT 4/4 | 10:00 AM | League | Sheehan | Foran | Sheehan High School - Sheehan HS Tennis Courts |
| SAT 4/4 | 10:00 AM | Non-League | Lyman Hall | Wilcox Tech | Lyman Hall High School - Tennis Courts |
| SAT 4/4 | 10:30 PM | League | Portland | Lyme-Old Lyme | Portland High School - Tennis Courts |
| SAT 4/4 | 11:00 AM | League | Torrington | Kennedy | Torrington High School - Tennis Courts |
| SAT 4/4 | 11:00 AM | League | West Haven | East Haven | West Haven High School - West Haven Tennis Courts |
| SAT 4/4 | 11:00 AM | Non-League | Bridgeport Central | Jonathan Law | Bridgeport Central High School - Central High School Tennis Courts |
| SAT 4/4 | 12:00 PM | League | Wilby | Seymour | Wilby High School - Dave Krill Tennis Courts at WHS |
| SAT 4/4 | 12:00 PM | Non-League | Waterford | Guilford | Waterford High School - Tennis Courts - WHS |
| SAT 4/4 | 12:01 AM | League | Woodland | Holy Cross | Woodland High School - Tennis Courts |
| SAT 4/4 | 3:45 PM | League | Naugatuck | Wolcott | Naugatuck High School - Tennis Courts |
| MON 4/6 | 12:01 AM | League | Woodstock Academy | Ledyard | Pomfret School - Field House |
| MON 4/6 | 3:30 PM | League | Kennedy | Wilby | John F. Kennedy High School - Chase Park |
| MON 4/6 | 3:30 PM | League | Wolcott | Woodland | Wolcott High School - WHS Tennis Courts |
| MON 4/6 | 3:45 PM | League | Amity | Shelton | Amity Regional High School - Tennis Courts |
| MON 4/6 | 3:45 PM | League | Berlin | RHAM | Berlin High School - Tennis Courts |
| MON 4/6 | 3:45 PM | League | Bloomfield | Plainville | Carmen Arace Middle School - Tennis Courts |
| MON 4/6 | 3:45 PM | League | Coginchaug | North Branford | Coginchaug Regional High School - Tennis Courts @ CRHS |
| MON 4/6 | 3:45 PM | League | Conard | Middletown | Conard High School - Tennis Courts |
| MON 4/6 | 3:45 PM | League | Fitch | East Lyme | Fitch High School - Main Tennis Courts |
| MON 4/6 | 3:45 PM | League | Glastonbury | Maloney | Glastonbury High School - Tennis Courts |
| MON 4/6 | 3:45 PM | League | Haddam Killingworth | Morgan | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| MON 4/6 | 3:45 PM | League | Housatonic Regional | Shepaug Valley | Housatonic Valley Regional High - Tennis Courts |
| MON 4/6 | 3:45 PM | League | Jonathan Law | North Haven | Jonathan Law High School - Tennis Courts |
| MON 4/6 | 3:45 PM | League | Killingly | NFA | Killingly High School - Tennis Courts |
| MON 4/6 | 3:45 PM | League | Lewis Mills | Bristol Eastern | Lewis Mills High School - Tennis Courts |
| MON 4/6 | 3:45 PM | League | Manchester | Bristol Central | Manchester High School - Manchester |
| MON 4/6 | 3:45 PM | League | Platt | Northwest Catholic | Platt High School - Tennis Court |
| MON 4/6 | 3:45 PM | League | Rocky Hill | Simsbury | Rocky Hill High School - Tennis Courts |
| MON 4/6 | 3:45 PM | League | South Windsor | East Hartford | South Windsor High School - Wapping Tennis Courts |
| MON 4/6 | 3:45 PM | League | Southington | Avon | Southington High School - Tennis Courts |
| MON 4/6 | 3:45 PM | League | St. Bernard | Montville | St. Bernard School - Tennis Courts |
| MON 4/6 | 3:45 PM | League | Stonington | Waterford | Stonington High School - SHS Tennis Courts |
| MON 4/6 | 3:45 PM | League | Tolland | New Britain | Tolland High School - Tennis Courts |
| MON 4/6 | 3:45 PM | League | Gilbert | Thomaston | Walker Field - Tennis Courts |
| MON 4/6 | 3:45 PM | League | Grasso Tech | Prince Tech | Washington Park - Washington Park Tennis Courts |
| MON 4/6 | 3:45 PM | League | Mercy | Sacred Heart Academy | Wesleyan University - Tennis Courts |
| MON 4/6 | 3:45 PM | League | Wethersfield | Farmington | Wethersfield High School - Tennis Courts |
| MON 4/6 | 3:45 PM | League | East Catholic | Enfield | Wickham Park - Wickham Park |
| MON 4/6 | 3:45 PM | League | Windsor | E.O. Smith | Windsor High School - Tennis Courts |
| MON 4/6 | 3:45 PM | Non-League | Abbott Tech | Bethel | WCSU O'Neill Center - Tennis Courts |
| MON 4/6 | 4:00 PM | League | Cromwell | East Hampton | Cromwell Middle School - Waterous Park Tennis Courts |
| MON 4/6 | 4:00 PM | League | Danbury | Trumbull | Danbury High School - DHS Tennis Courts |
| MON 4/6 | 4:00 PM | League | Fairfield Warde | St. Joseph | Fairfield Warde High School - Blake Courts |
| MON 4/6 | 4:00 PM | League | Norwalk | Wilton | Grassroots Tennis and Education - Grassroots Tennis Courts |
| MON 4/6 | 4:00 PM | League | Greenwich | Fairfield Ludlowe | Greenwich High School - GHS Tennis Courts |
| MON 4/6 | 4:00 PM | League | Lakeview | Northwestern | Lakeview Regional High School - Tennis Courts |
| MON 4/6 | 4:00 PM | League | Lyman Memorial | New London | Lyman Memorial High School - Tennis Courts |
| MON 4/6 | 4:00 PM | League | Lyme-Old Lyme | Valley Regional | Lyme-Old Lyme High School - Tennis Courts |
| MON 4/6 | 4:00 PM | League | Newington | Hall | Newington High School - Tennis Courts |
| MON 4/6 | 4:00 PM | League | Stamford | Brien McMahon | Stamford High School - SHS Tennis Courts |
| MON 4/6 | 4:00 PM | League | Staples | New Canaan | Staples High School - Staples Tennis Courts |
| MON 4/6 | 4:00 PM | League | Westhill | Darien | Westhill High School - Westhill Tennis Courts |
| MON 4/6 | 5:00 PM | League | Bridgeport Central | Ridgefield | Bridgeport Central High School - Central High School Tennis Courts |
| TUE 4/7 | 3:30 PM | League | Seymour | Crosby | Seymour High School - Tennis |
| TUE 4/7 | 3:45 PM | League | Guilford | Foran | Guilford High School - GHS Tennis Courts |
| TUE 4/7 | 3:45 PM | League | Jonathan Law | Career Magnet | Jonathan Law High School - Tennis Courts |
| TUE 4/7 | 3:45 PM | League | Montville | Windham | Montville High School - Tennis Courts |
| TUE 4/7 | 3:45 PM | League | Sheehan | Branford | Sheehan High School - Sheehan HS Tennis Courts |
| TUE 4/7 | 3:45 PM | League | West Haven | Hamden | West Haven High School - West Haven Tennis Courts |
| TUE 4/7 | 4:00 PM | League | Brien McMahon | Staples | Brien McMahon High School - Tennis Courts |
| TUE 4/7 | 4:00 PM | League | Darien | Wilton | Darien High School - DHS Tennis Courts |
| TUE 4/7 | 4:00 PM | League | Fairfield Ludlowe | Danbury | Fairfield Ludlowe High School - Tennis Courts |
| TUE 4/7 | 4:00 PM | League | Greenwich | St. Joseph | Greenwich High School - GHS Tennis Courts |
| TUE 4/7 | 4:00 PM | League | New Canaan | Norwalk | New Canaan HS - NCHS Tennis Courts |
| TUE 4/7 | 4:00 PM | League | Ridgefield | Westhill | Ridgefield High School - RHS Tennis Courts |
| TUE 4/7 | 4:00 PM | League | Stamford | Bridgeport Central | Stamford High School - SHS Tennis Courts |
| TUE 4/7 | 4:00 PM | League | Trumbull | Fairfield Warde | Trumbull High School - Tennis Courts |
| TUE 4/7 | 4:00 PM | Non-League | Coventry | Granby Memorial | Coventry High School - tennis courts |
| TUE 4/7 | 4:00 PM | Non-League | Masuk | Canton | Wolfe Park - Tennis Courts |
| WED 4/8 | 12:01 AM | League | Woodland | Kennedy | Woodland High School - Tennis Courts |
| WED 4/8 | 3:30 PM | League | Wolcott | Crosby | Wolcott High School - WHS Tennis Courts |
| WED 4/8 | 3:45 PM | League | Berlin | Newington | Berlin High School - Tennis Courts |
| WED 4/8 | 3:45 PM | League | Bristol Central | Rocky Hill | Bristol Central High School - Tennis Courts |
| WED 4/8 | 3:45 PM | League | Bristol Eastern | Plainville | Bristol Eastern High School - Tennis Court |
| WED 4/8 | 3:45 PM | League | Bloomfield | Platt | Carmen Arace Middle School - Tennis Courts |
| WED 4/8 | 3:45 PM | League | Cheshire | Sheehan | Cheshire High School - Tennis Courts |
| WED 4/8 | 3:45 PM | League | Coginchaug | Portland | Coginchaug Regional High School - Tennis Courts @ CRHS |
| WED 4/8 | 3:45 PM | League | Lyman Hall | Foran | Doolittle Park - Doolittle Tennis Courts |
| WED 4/8 | 3:45 PM | League | E.O. Smith | Manchester | E.O. Smith High School - Tennis Courts |
| WED 4/8 | 3:45 PM | League | East Hartford | Glastonbury | East Hartford High School - Tennis Courts |
| WED 4/8 | 3:45 PM | League | East Haven | Amity | East Haven High School - Tennis Court |
| WED 4/8 | 3:45 PM | League | Hall | Avon | Hall High School - Tennis Courts |
| WED 4/8 | 3:45 PM | League | Hamden | North Haven | Hamden Middle School - Tennis Courts |
| WED 4/8 | 3:45 PM | League | Killingly | East Lyme | Killingly High School - Tennis Courts |
| WED 4/8 | 3:45 PM | League | Maloney | Wethersfield | Maloney High School - Tennis Courts |
| WED 4/8 | 3:45 PM | League | Middletown | East Catholic | Middletown Tennis Courts - Beman Tennis Courts |
| WED 4/8 | 3:45 PM | League | Naugatuck | Ansonia | Naugatuck High School - Tennis Courts |
| WED 4/8 | 3:45 PM | League | New Britain | Conard | New Britain High School - tennis courts |
| WED 4/8 | 3:45 PM | League | Nonnewaug | Housatonic Regional | Nonnewaug High School - Tennis Courts |
| WED 4/8 | 3:45 PM | League | Norwich Tech | Grasso Tech | Norwich Technical High School - NTHS Outdoor Athletic Complex |
| WED 4/8 | 3:45 PM | League | NFA | Fitch | Rec Fields - Armstrong Tennis Courts |
| WED 4/8 | 3:45 PM | League | Shepaug Valley | Gilbert | Shepaug Valley High School - Shepaug Valley Tennis Courts |
| WED 4/8 | 3:45 PM | League | Simsbury | Windsor | Simsbury High School - Tennis Courts |
| WED 4/8 | 3:45 PM | League | South Windsor | Farmington | South Windsor High School - Wapping Tennis Courts |
| WED 4/8 | 3:45 PM | League | Southington | RHAM | Southington High School - Tennis Courts |
| WED 4/8 | 3:45 PM | League | St. Bernard | New London | St. Bernard School - Tennis Courts |
| WED 4/8 | 3:45 PM | League | Watertown | Wilby | TBA - TBA |
| WED 4/8 | 3:45 PM | League | Thomaston | Northwestern | Thomaston Nystrom Park - Nystroms Park courts |
| WED 4/8 | 3:45 PM | League | Northwest Catholic | Lewis Mills | University of Saint Joseph - West Hartford - Tennis Courts |
| WED 4/8 | 3:45 PM | League | Valley Regional | North Branford | Valley Regional High School - Tennis Courts |
| WED 4/8 | 3:45 PM | League | Waterford | Ledyard | Waterford High School - Tennis Courts - WHS |
| WED 4/8 | 3:45 PM | League | Weston | Joel Barlow | Weston High School - WHS Tennis Courts |
| WED 4/8 | 3:45 PM | Non-League | Bethel | Lakeview | Bethel High School - BHS Tennis Courts |
| WED 4/8 | 4:00 PM | League | East Hampton | Haddam Killingworth | East Hampton High School - Tennis Courts |
| WED 4/8 | 4:00 PM | League | Old Saybrook | Lyme-Old Lyme | Old Saybrook High School - Old Saybrook Tennis Courts |
| WED 4/8 | 4:15 PM | League | Stonington | Woodstock Academy | Stonington High School - SHS Tennis Courts |
| WED 4/8 | 5:00 AM | League | Enfield | Tolland | Enfield High School - EHS TENNIS COURTS |
| THU 4/9 | 3:45 PM | League | Bristol Eastern | Rocky Hill | Bristol Eastern High School - Tennis Court |
| THU 4/9 | 3:45 PM | League | Valley Regional | Portland | Valley Regional High School - Tennis Courts |
| THU 4/9 | 3:45 PM | League | West Haven | Jonathan Law | West Haven High School - West Haven Tennis Courts |
| THU 4/9 | 3:45 PM | League | Wethersfield | Hall | Wethersfield High School - Tennis Courts |
| THU 4/9 | 3:45 PM | Non-League | Masuk | Newtown | Wolfe Park - Tennis Courts |
| THU 4/9 | 4:00 PM | League | Darien | Stamford | Darien High School - DHS Tennis Courts |
| THU 4/9 | 4:00 PM | League | Ellington | Windsor Locks | Ellington High School - Tennis Courts |
| THU 4/9 | 4:00 PM | League | Fairfield Warde | Bridgeport Central | Fairfield Warde High School - Blake Courts |
| THU 4/9 | 4:00 PM | League | Norwalk | Staples | Grassroots Tennis and Education - Grassroots Tennis Courts |
| THU 4/9 | 4:00 PM | League | New Canaan | Fairfield Ludlowe | New Canaan HS - NCHS Tennis Courts |
| THU 4/9 | 4:00 PM | League | Rockville | Granby Memorial | Rockville High School - RHS Tennis Courts |
| THU 4/9 | 4:00 PM | League | St. Joseph | Ridgefield | St. Joseph High School - Tennis Courts |
| THU 4/9 | 4:00 PM | League | Trumbull | Brien McMahon | Trumbull High School - Tennis Courts |
| THU 4/9 | 4:00 PM | League | Westhill | Danbury | Westhill High School - Westhill Tennis Courts |
| THU 4/9 | 4:00 PM | League | Wilton | Greenwich | Wilton High School - Allen Meadow |
| FRI 4/10 | 12:00 PM | League | Wilby | Crosby | Wilby High School - Dave Krill Tennis Courts at WHS |
| FRI 4/10 | 12:01 AM | League | Prince Tech | Norwich Tech | TBA - TBA |
| FRI 4/10 | 12:01 AM | League | Woodland | Watertown | Woodland High School - Tennis Courts |
| FRI 4/10 | 3:30 PM | League | Torrington | Seymour | Torrington High School - Tennis Courts |
| FRI 4/10 | 3:45 PM | League | Amity | Mercy | Amity Regional High School - Tennis Courts |
| FRI 4/10 | 3:45 PM | League | Bristol Central | Southington | Bristol Central High School - Tennis Courts |
| FRI 4/10 | 3:45 PM | League | Lyman Hall | Sheehan | Doolittle Park - Doolittle Tennis Courts |
| FRI 4/10 | 3:45 PM | League | East Hartford | Rockville | East Hartford High School - Tennis Courts |
| FRI 4/10 | 3:45 PM | League | East Haven | North Haven | East Haven High School - Tennis Court |
| FRI 4/10 | 3:45 PM | League | Fitch | Waterford | Fitch High School - Main Tennis Courts |
| FRI 4/10 | 3:45 PM | League | Foran | Branford | Foran High School - Foran Tennis Courts |
| FRI 4/10 | 3:45 PM | League | Guilford | Lauralton Hall | Guilford High School - GHS Tennis Courts |
| FRI 4/10 | 3:45 PM | League | Haddam Killingworth | Cromwell | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| FRI 4/10 | 3:45 PM | League | Housatonic Regional | Gilbert | Housatonic Valley Regional High - Tennis Courts |
| FRI 4/10 | 3:45 PM | League | Kennedy | Ansonia | John F. Kennedy High School - Chase Park |
| FRI 4/10 | 3:45 PM | League | Ledyard | New London | Ledyard High School - Tennis Courts |
| FRI 4/10 | 3:45 PM | League | Montville | Woodstock Academy | Montville High School - Tennis Courts |
| FRI 4/10 | 3:45 PM | League | Nonnewaug | Thomaston | Nonnewaug High School - Tennis Courts |
| FRI 4/10 | 3:45 PM | League | North Branford | Old Saybrook | North Branford - NBHS Tennis Courts |
| FRI 4/10 | 3:45 PM | League | Northwestern | Granby Memorial | Northwestern Regional H.S. - Tennis Courts |
| FRI 4/10 | 3:45 PM | League | Shelton | Hamden | Shelton High School - Tennis Courts |
| FRI 4/10 | 3:45 PM | League | Shepaug Valley | Lakeview | Shepaug Valley High School - Shepaug Valley Tennis Courts |
| FRI 4/10 | 3:45 PM | League | St. Bernard | Lyman Memorial | St. Bernard School - Tennis Courts |
| FRI 4/10 | 3:45 PM | League | Grasso Tech | Wilcox Tech | Washington Park - Washington Park Tennis Courts |
| FRI 4/10 | 3:45 PM | League | East Catholic | Conard | Wickham Park - Wickham Park |
| FRI 4/10 | 3:45 PM | League | Windham | Killingly | Windham High School - WHS Courts |
| FRI 4/10 | 3:45 PM | League | Masuk | Joel Barlow | Wolfe Park - Tennis Courts |
| FRI 4/10 | 4:00 PM | League | Lyme-Old Lyme | Morgan | Lyme-Old Lyme High School - Tennis Courts |
| FRI 4/10 | 4:00 PM | League | Westbrook | East Hampton | Westbrook High School - Westbrook HS / MS Tennis Courts |
| SAT 4/11 | 11:00 AM | League | Westbrook | Old Saybrook | Westbrook High School - Westbrook HS / MS Tennis Courts |
| MON 4/13 | 10:00 AM | Non-League | Wilcox Tech | East Haven | Wilcox Tech - Tennis Courts |
| MON 4/13 | 11:00 AM | League | Rockville | Bolton | Rockville High School - RHS Tennis Courts |
| MON 4/13 | 3:30 PM | League | Kennedy | Holy Cross | John F. Kennedy High School - Chase Park |
| MON 4/13 | 3:30 PM | League | Seymour | Naugatuck | Seymour High School - Tennis |
| MON 4/13 | 3:30 PM | League | Torrington | Woodland | Torrington High School - Tennis Courts |
| MON 4/13 | 3:45 PM | League | Bethel | Pomperaug | Bethel High School - BHS Tennis Courts |
| MON 4/13 | 3:45 PM | League | Brookfield | New Fairfield | Brookfield High School - BHS Tennis Courts |
| MON 4/13 | 3:45 PM | League | Bunnell | Masuk | Bunnell HS - Bunnell Tennis Courts |
| MON 4/13 | 3:45 PM | League | Cheshire | Lyman Hall | Cheshire High School - Tennis Courts |
| MON 4/13 | 3:45 PM | League | East Hartford | Avon | East Hartford High School - Tennis Courts |
| MON 4/13 | 3:45 PM | League | Farmington | Berlin | Farmington High School - Large Gymnasium |
| MON 4/13 | 3:45 PM | League | Foran | Daniel Hand | Foran High School - Foran Tennis Courts |
| MON 4/13 | 3:45 PM | League | Hamden | Amity | Hamden Middle School - Tennis Courts |
| MON 4/13 | 3:45 PM | League | Joel Barlow | Immaculate | Joel Barlow High School - Tennis Courts |
| MON 4/13 | 3:45 PM | League | Jonathan Law | Sacred Heart Academy | Jonathan Law High School - Tennis Courts |
| MON 4/13 | 3:45 PM | League | Lewis Mills | Bristol Central | Lewis Mills High School - Tennis Courts |
| MON 4/13 | 3:45 PM | League | Stratford | Bassick | Penders Field - Tennis Courts |
| MON 4/13 | 3:45 PM | League | Sheehan | Lauralton Hall | Sheehan High School - Sheehan HS Tennis Courts |
| MON 4/13 | 3:45 PM | League | Shelton | North Haven | Shelton High School - Tennis Courts |
| MON 4/13 | 3:45 PM | League | Southington | E.O. Smith | Southington High School - Tennis Courts |
| MON 4/13 | 3:45 PM | League | Tolland | Middletown | Tolland High School - Tennis Courts |
| MON 4/13 | 3:45 PM | League | Mercy | West Haven | Wesleyan University - Tennis Courts |
| MON 4/13 | 3:45 PM | League | Weston | Newtown | Weston High School - WHS Tennis Courts |
| MON 4/13 | 3:45 PM | League | Wilby | Wolcott | Wilby High School - Dave Krill Tennis Courts at WHS |
| MON 4/13 | 3:45 PM | League | Windsor | Platt | Windsor High School - Tennis Courts |
| MON 4/13 | 4:00 PM | League | Danbury | Brien McMahon | Danbury High School - DHS Tennis Courts |
| MON 4/13 | 4:00 PM | League | Darien | St. Joseph | Darien High School - DHS Tennis Courts |
| MON 4/13 | 4:00 PM | League | Fairfield Warde | New Canaan | Fairfield Warde High School - Blake Courts |
| MON 4/13 | 4:00 PM | League | Granby Memorial | Suffield | Granby Memorial High School - Tennis Courts |
| MON 4/13 | 4:00 PM | League | Norwalk | Ridgefield | Grassroots Tennis and Education - Grassroots Tennis Courts |
| MON 4/13 | 4:00 PM | League | Lyme-Old Lyme | East Hampton | Lyme-Old Lyme High School - Tennis Courts |
| MON 4/13 | 4:00 PM | League | Morgan | North Branford | Morgan School - Tennis Courts |
| MON 4/13 | 4:00 PM | League | Staples | Stamford | Staples High School - Staples Tennis Courts |
| MON 4/13 | 4:00 PM | League | Westhill | Fairfield Ludlowe | Westhill High School - Westhill Tennis Courts |
| MON 4/13 | 4:00 PM | League | Wilton | Trumbull | Wilton High School - Allen Meadow |
| MON 4/13 | 5:00 PM | League | Bridgeport Central | Greenwich | Bridgeport Central High School - Central High School Tennis Courts |
| TUE 4/14 | 11:00 AM | League | East Lyme | Daniel Hand | East Lyme High School - Tennis Courts |
| TUE 4/14 | 2:00 PM | Non-League | Abbott Tech | Immaculate | WCSU O'Neill Center - Tennis Courts |
| TUE 4/14 | 3:45 PM | League | Bristol Eastern | Simsbury | Bristol Eastern High School - Tennis Court |
| TUE 4/14 | 3:45 PM | League | E.O. Smith | Plainville | E.O. Smith High School - Tennis Courts |
| TUE 4/14 | 3:45 PM | League | Glastonbury | Newington | Glastonbury High School - Tennis Courts |
| TUE 4/14 | 3:45 PM | League | Manchester | Bloomfield | Manchester High School - Manchester |
| TUE 4/14 | 3:45 PM | League | New Britain | Enfield | New Britain High School - tennis courts |
| TUE 4/14 | 3:45 PM | League | RHAM | Maloney | RHAM High School - Tennis Courts |
| TUE 4/14 | 3:45 PM | League | Rocky Hill | Northwest Catholic | Rocky Hill High School |
| TUE 4/14 | 3:45 PM | Non-League | Mercy | Wolcott | Wesleyan University - Tennis Courts |
| TUE 4/14 | 4:00 PM | League | Brien McMahon | Fairfield Ludlowe | Brien McMahon High School - Tennis Courts |
| TUE 4/14 | 4:00 PM | League | Danbury | Wilton | Danbury High School - DHS Tennis Courts |
| TUE 4/14 | 4:00 PM | League | Greenwich | New Canaan | Greenwich High School - GHS Tennis Courts |
| TUE 4/14 | 4:00 PM | League | Morgan | Westbrook | Morgan School - Tennis Courts |
| TUE 4/14 | 4:00 PM | League | St. Joseph | Norwalk | St. Joseph High School - Tennis Courts |
| TUE 4/14 | 4:00 PM | League | Stamford | Ridgefield | Stamford High School - SHS Tennis Courts |
| TUE 4/14 | 4:00 PM | League | Staples | Darien | Staples High School - Staples Tennis Courts |
| TUE 4/14 | 4:00 PM | League | Westhill | Fairfield Warde | Westhill High School - Westhill Tennis Courts |
| TUE 4/14 | 5:00 PM | League | Bridgeport Central | Trumbull | Bridgeport Central High School - Central High School Tennis Courts |
| WED 4/15 | 3:30 PM | League | Seymour | Kennedy | Seymour High School - Tennis |
| WED 4/15 | 3:45 PM | League | Amity | North Haven | Amity Regional High School - Tennis Courts |
| WED 4/15 | 3:45 PM | League | Branford | Hamden | Branford High School - Tennis Courts |
| WED 4/15 | 3:45 PM | League | Bunnell | New Milford | Bunnell HS - Bunnell Tennis Courts |
| WED 4/15 | 3:45 PM | League | Cromwell | Lyme-Old Lyme | Cromwell Middle School - Waterous Park Tennis Courts |
| WED 4/15 | 3:45 PM | League | Lyman Hall | Shelton | Doolittle Park - Doolittle Tennis Courts |
| WED 4/15 | 3:45 PM | League | East Haven | Career Magnet | East Haven High School - Tennis Court |
| WED 4/15 | 3:45 PM | League | Platt Tech | Abbott Tech | Eisenhower Park - Eisenhower Park |
| WED 4/15 | 3:45 PM | League | Guilford | Daniel Hand | Guilford High School - GHS Tennis Courts |
| WED 4/15 | 3:45 PM | League | Haddam Killingworth | Westbrook | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| WED 4/15 | 3:45 PM | League | Naugatuck | Woodland | Naugatuck High School - Tennis Courts |
| WED 4/15 | 3:45 PM | League | New Fairfield | Immaculate | New Fairfield High School - Tennis Courts |
| WED 4/15 | 3:45 PM | League | Newtown | Brookfield | Newtown High School - NHS Tennis Courts |
| WED 4/15 | 3:45 PM | League | North Branford | East Hampton | North Branford - NBHS Tennis Courts |
| WED 4/15 | 3:45 PM | League | Stratford | Bethel | Penders Field - Tennis Courts |
| WED 4/15 | 3:45 PM | League | Pomperaug | Weston | Pomperaug High School - PHS Tennis Courts |
| WED 4/15 | 3:45 PM | League | Watertown | Holy Cross | TBA - TBA |
| WED 4/15 | 3:45 PM | League | Notre Dame Prep | Bassick | Veteran's Park - Bridgeport - Tennis Courts |
| WED 4/15 | 3:45 PM | League | Mercy | Jonathan Law | Wesleyan University - Tennis Courts |
| WED 4/15 | 3:45 PM | League | West Haven | Sheehan | West Haven High School - West Haven Tennis Courts |
| WED 4/15 | 3:45 PM | League | Wethersfield | Rockville | Wethersfield High School - Tennis Courts |
| WED 4/15 | 3:45 PM | League | Wilby | Ansonia | Wilby High School - Dave Krill Tennis Courts at WHS |
| WED 4/15 | 3:45 PM | League | Windsor Locks | Coventry | Windsor Locks High School - Tennis Court |
| WED 4/15 | 3:45 PM | Non-League | Windham | Norwich Tech | Windham High School - WHS Courts |
| WED 4/15 | 4:00 PM | League | Old Saybrook | Coginchaug | Old Saybrook High School - Old Saybrook Tennis Courts |
| WED 4/15 | 4:00 PM | Non-League | Granby Memorial | Bristol Central | Granby Memorial High School - Tennis Courts |
| THU 4/16 | 11:00 AM | Non-League | Rockville | RHAM | Rockville High School - RHS Tennis Courts |
| THU 4/16 | 3:45 PM | League | Lyman Hall | Jonathan Law | Doolittle Park - Doolittle Tennis Courts |
| THU 4/16 | 4:00 PM | League | Brien McMahon | Westhill | Brien McMahon High School - Tennis Courts |
| THU 4/16 | 4:00 PM | League | Fairfield Ludlowe | Norwalk | Fairfield Ludlowe High School - Tennis Courts |
| THU 4/16 | 4:00 PM | League | Greenwich | Staples | Greenwich High School - GHS Tennis Courts |
| THU 4/16 | 4:00 PM | League | Ridgefield | Fairfield Warde | Ridgefield High School - RHS Tennis Courts |
| THU 4/16 | 4:00 PM | League | St. Joseph | Bridgeport Central | St. Joseph High School - Tennis Courts |
| THU 4/16 | 4:00 PM | League | Stamford | Danbury | Stamford High School - SHS Tennis Courts |
| THU 4/16 | 4:00 PM | League | Trumbull | Darien | Trumbull High School - Tennis Courts |
| THU 4/16 | 4:15 PM | League | New Canaan | Wilton | New Canaan HS - Conner Field, New Cannan |
| FRI 4/17 | 3:45 PM | League | Bethel | Newtown | Bethel High School - BHS Tennis Courts |
| FRI 4/17 | 3:45 PM | League | Brookfield | Bunnell | Brookfield High School - BHS Tennis Courts |
| FRI 4/17 | 3:45 PM | League | Foran | Sheehan | Foran High School - Foran Tennis Courts |
| FRI 4/17 | 3:45 PM | League | New Fairfield | Pomperaug | New Fairfield High School - Tennis Courts |
| FRI 4/17 | 3:45 PM | League | North Branford | Cromwell | North Branford - NBHS Tennis Courts |
| FRI 4/17 | 3:45 PM | League | Stratford | Masuk | Penders Field - Tennis Courts |
| FRI 4/17 | 3:45 PM | League | Notre Dame Prep | Immaculate | Veteran's Park - Bridgeport - Tennis Courts |
| FRI 4/17 | 4:00 PM | League | Lyme-Old Lyme | Haddam Killingworth | Lyme-Old Lyme High School - Tennis Courts |
| FRI 4/17 | 4:00 PM | League | Morgan | Coginchaug | Morgan School - Tennis Courts |
| SAT 4/18 | 1:00 PM | League | West Haven | Platt Tech | West Haven High School - West Haven Tennis Courts |
| SAT 4/18 | 10:00 AM | Non-League | Sheehan | Wilcox Tech | Sheehan High School - Sheehan HS Tennis Courts |
| SAT 4/18 | 11:00 AM | League | Cheshire | Guilford | Cheshire High School - Tennis Courts |
| MON 4/20 | 2:00 PM | League | Abbott Tech | Prince Tech | WCSU O'Neill Center - Tennis Courts |
| MON 4/20 | 3:30 PM | League | Avon | Newington | Avon Middle School - Thompson Brook School |
| MON 4/20 | 3:30 PM | League | Torrington | Wilby | Torrington High School - Tennis Courts |
| MON 4/20 | 3:30 PM | League | Wolcott | Watertown | Wolcott High School - WHS Tennis Courts |
| MON 4/20 | 3:30 PM | League | Woodland | St. Paul Catholic | Woodland High School - Tennis Courts |
| MON 4/20 | 3:45 PM | League | Berlin | Southington | Berlin High School - Tennis Courts |
| MON 4/20 | 3:45 PM | League | Brookfield | Notre Dame Prep | Brookfield High School - BHS Tennis Courts |
| MON 4/20 | 3:45 PM | League | Bunnell | Weston | Bunnell HS - Bunnell Tennis Courts |
| MON 4/20 | 3:45 PM | League | Coginchaug | East Hampton | Coginchaug Regional High School - Tennis Courts @ CRHS |
| MON 4/20 | 3:45 PM | League | Lyman Hall | Sacred Heart Academy | Doolittle Park - Doolittle Tennis Courts |
| MON 4/20 | 3:45 PM | League | E.O. Smith | Rocky Hill | E.O. Smith High School - Tennis Courts |
| MON 4/20 | 3:45 PM | League | East Haven | Hamden | East Haven High School - Tennis Court |
| MON 4/20 | 3:45 PM | League | Platt Tech | Grasso Tech | Eisenhower Park - Eisenhower Park |
| MON 4/20 | 3:45 PM | League | Farmington | Glastonbury | Farmington High School - Large Gymnasium |
| MON 4/20 | 3:45 PM | League | Foran | Shelton | Foran High School - Foran Tennis Courts |
| MON 4/20 | 3:45 PM | League | Guilford | Mercy | Guilford High School - GHS Tennis Courts |
| MON 4/20 | 3:45 PM | League | Hall | RHAM | Hall High School - Tennis Courts |
| MON 4/20 | 3:45 PM | League | Joel Barlow | Pomperaug | Joel Barlow High School - Tennis Courts |
| MON 4/20 | 3:45 PM | League | Killingly | Woodstock Academy | Killingly High School - Tennis Courts |
| MON 4/20 | 3:45 PM | League | Maloney | East Hartford | Maloney High School - Tennis Courts |
| MON 4/20 | 3:45 PM | League | Middletown | New Britain | Middletown Tennis Courts - Beman Tennis Courts |
| MON 4/20 | 3:45 PM | League | Naugatuck | Holy Cross | Naugatuck High School - Tennis Courts |
| MON 4/20 | 3:45 PM | League | New Fairfield | Newtown | New Fairfield High School - Tennis Courts |
| MON 4/20 | 3:45 PM | League | Nonnewaug | Northwestern | Nonnewaug High School - Tennis Courts |
| MON 4/20 | 3:45 PM | League | North Branford | Haddam Killingworth | North Branford - NBHS Tennis Courts |
| MON 4/20 | 3:45 PM | League | North Haven | Cheshire | North Haven Athletic Complex - Tennis Courts |
| MON 4/20 | 3:45 PM | League | Norwich Tech | Wilcox Tech | Norwich Technical High School - NTHS Outdoor Athletic Complex |
| MON 4/20 | 3:45 PM | League | Plainville | Lewis Mills | Plainville High School - PHS Tennis Courts |
| MON 4/20 | 3:45 PM | League | Platt | Bristol Eastern | Platt High School - Tennis Court |
| MON 4/20 | 3:45 PM | League | NFA | Ledyard | Rec Fields - Armstrong Tennis Courts |
| MON 4/20 | 3:45 PM | League | Immaculate | Stratford | Rogers Park - Tennis Courts |
| MON 4/20 | 3:45 PM | League | Shepaug Valley | Thomaston | Shepaug Valley High School - Shepaug Valley Tennis Courts |
| MON 4/20 | 3:45 PM | League | Simsbury | Bristol Central | Simsbury High School - Tennis Courts |
| MON 4/20 | 3:45 PM | League | St. Bernard | Fitch | St. Bernard School - Tennis Courts |
| MON 4/20 | 3:45 PM | League | Northwest Catholic | Bloomfield | University of Saint Joseph - West Hartford - Tennis Courts |
| MON 4/20 | 3:45 PM | League | Gilbert | Lakeview | Walker Field - Tennis Courts |
| MON 4/20 | 3:45 PM | League | Waterford | Montville | Waterford High School - Tennis Courts - WHS |
| MON 4/20 | 3:45 PM | League | Wethersfield | South Windsor | Wethersfield High School - Tennis Courts |
| MON 4/20 | 3:45 PM | League | East Catholic | Tolland | Wickham Park - Wickham Park |
| MON 4/20 | 3:45 PM | League | Windham | Stonington | Windham High School - WHS Courts |
| MON 4/20 | 3:45 PM | League | Windsor | Manchester | Windsor High School - Tennis Courts |
| MON 4/20 | 3:45 PM | League | Windsor Locks | Bolton | Windsor Locks High School - Tennis Court |
| MON 4/20 | 4:00 PM | League | Darien | Bridgeport Central | Darien High School - DHS Tennis Courts |
| MON 4/20 | 4:00 PM | League | Fairfield Ludlowe | St. Joseph | Fairfield Ludlowe High School - Tennis Courts |
| MON 4/20 | 4:00 PM | League | Fairfield Warde | Danbury | Fairfield Warde High School - Blake Courts |
| MON 4/20 | 4:00 PM | League | Granby Memorial | Ellington | Granby Memorial High School - Tennis Courts |
| MON 4/20 | 4:00 PM | League | Norwalk | Westhill | Grassroots Tennis and Education - Grassroots Tennis Courts |
| MON 4/20 | 4:00 PM | League | Lyme-Old Lyme | Westbrook | Lyme-Old Lyme High School - Tennis Courts |
| MON 4/20 | 4:00 PM | League | Morgan | Valley Regional | Morgan School - Tennis Courts |
| MON 4/20 | 4:00 PM | League | New Canaan | Stamford | New Canaan HS - NCHS Tennis Courts |
| MON 4/20 | 4:00 PM | League | New London | Lyman Memorial | New London High School - NLHS Tennis Courts |
| MON 4/20 | 4:00 PM | League | Ridgefield | Brien McMahon | Ridgefield High School - RHS Tennis Courts |
| MON 4/20 | 4:00 PM | League | Trumbull | Greenwich | Trumbull High School - Tennis Courts |
| MON 4/20 | 4:00 PM | League | Wilton | Staples | Wilton High School - Allen Meadow |
| MON 4/20 | 5:00 AM | League | Enfield | Conard | Enfield High School - EHS TENNIS COURTS |
| TUE 4/21 | 3:45 PM | League | Branford | West Haven | Branford High School - Tennis Courts |
| TUE 4/21 | 3:45 PM | League | St. Bernard | Windham | St. Bernard School - Tennis Courts |
| TUE 4/21 | 3:45 PM | Non-League | East Granby | Coventry | East Granby High School - EGHS Tennis Courts |
| TUE 4/21 | 4:00 PM | League | Brien McMahon | New Canaan | Brien McMahon High School - Tennis Courts |
| TUE 4/21 | 4:00 PM | League | Danbury | Norwalk | Danbury High School - DHS Tennis Courts |
| TUE 4/21 | 4:00 PM | League | Fairfield Ludlowe | Ridgefield | Fairfield Ludlowe High School - Tennis Courts |
| TUE 4/21 | 4:00 PM | League | Greenwich | Darien | Greenwich High School - GHS Tennis Courts |
| TUE 4/21 | 4:00 PM | League | Old Saybrook | Portland | Old Saybrook High School - Old Saybrook Tennis Courts |
| TUE 4/21 | 4:00 PM | League | Stamford | Trumbull | Stamford High School - SHS Tennis Courts |
| TUE 4/21 | 4:00 PM | League | Staples | Fairfield Warde | Staples High School - Staples Tennis Courts |
| TUE 4/21 | 4:00 PM | League | Westhill | St. Joseph | Westhill High School - Westhill Tennis Courts |
| TUE 4/21 | 5:00 PM | League | Bridgeport Central | Wilton | Bridgeport Central High School - Central High School Tennis Courts |
| WED 4/22 | 12:01 AM | League | Woodstock Academy | Waterford | Pomfret School - Field House |
| WED 4/22 | 12:01 AM | League | Prince Tech | Grasso Tech | TBA - TBA |
| WED 4/22 | 3:30 PM | League | Seymour | Holy Cross | Seymour High School - Tennis |
| WED 4/22 | 3:30 PM | League | Torrington | Wolcott | Torrington High School - Tennis Courts |
| WED 4/22 | 3:45 PM | League | Bethel | New Fairfield | Bethel High School - BHS Tennis Courts |
| WED 4/22 | 3:45 PM | League | Cromwell | Coginchaug | Cromwell Middle School - Waterous Park Tennis Courts |
| WED 4/22 | 3:45 PM | League | East Lyme | NFA | East Lyme High School - Tennis Courts |
| WED 4/22 | 3:45 PM | League | Guilford | Amity | Guilford High School - GHS Tennis Courts |
| WED 4/22 | 3:45 PM | League | Haddam Killingworth | Portland | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| WED 4/22 | 3:45 PM | League | Kennedy | Watertown | John F. Kennedy High School - Chase Park |
| WED 4/22 | 3:45 PM | League | Jonathan Law | Cheshire | Jonathan Law High School - Tennis Courts |
| WED 4/22 | 3:45 PM | League | Ledyard | Stonington | Ledyard High School - Tennis Courts |
| WED 4/22 | 3:45 PM | League | Newtown | Joel Barlow | Newtown High School - NHS Tennis Courts |
| WED 4/22 | 3:45 PM | League | Northwestern | Shepaug Valley | Northwestern Regional H.S. - Tennis Courts |
| WED 4/22 | 3:45 PM | League | Norwich Tech | Platt Tech | Norwich Technical High School - NTHS Outdoor Athletic Complex |
| WED 4/22 | 3:45 PM | League | Stratford | Brookfield | Penders Field - Tennis Courts |
| WED 4/22 | 3:45 PM | League | Pomperaug | Bunnell | Pomperaug High School - PHS Tennis Courts |
| WED 4/22 | 3:45 PM | League | Sheehan | Hamden | Sheehan High School - Sheehan HS Tennis Courts |
| WED 4/22 | 3:45 PM | League | Shelton | East Haven | Shelton High School - Tennis Courts |
| WED 4/22 | 3:45 PM | League | South Windsor | Southington | South Windsor High School - Wapping Tennis Courts |
| WED 4/22 | 3:45 PM | League | Thomaston | Housatonic Regional | Thomaston Nystrom Park - Nystroms Park courts |
| WED 4/22 | 3:45 PM | League | Mercy | Lauralton Hall | Wesleyan University - Tennis Courts |
| WED 4/22 | 3:45 PM | League | Weston | Notre Dame Prep | Weston High School - WHS Tennis Courts |
| WED 4/22 | 3:45 PM | League | Wethersfield | Granby Memorial | Wethersfield High School - Tennis Courts |
| WED 4/22 | 3:45 PM | League | Wilby | St. Paul Catholic | Wilby High School - Dave Krill Tennis Courts at WHS |
| WED 4/22 | 3:45 PM | League | Windsor Locks | Rockville | Windsor Locks High School - Tennis Court |
| WED 4/22 | 3:45 PM | Non-League | East Granby | Bolton | East Granby High School - EGHS Tennis Courts |
| WED 4/22 | 4:00 PM | League | East Hampton | Valley Regional | East Hampton High School - Tennis Courts |
| WED 4/22 | 4:00 PM | League | Ellington | Suffield | Ellington High School - Tennis Courts |
| WED 4/22 | 4:00 PM | League | Lakeview | Nonnewaug | Lakeview Regional High School - Tennis Courts |
| WED 4/22 | 4:00 PM | League | Lyman Memorial | Montville | Lyman Memorial High School - Tennis Courts |
| WED 4/22 | 4:00 PM | League | New London | Killingly | New London High School - NLHS Tennis Courts |
| WED 4/22 | 4:00 PM | League | Newington | East Catholic | Newington High School - Tennis Courts |
| WED 4/22 | 4:00 PM | League | Old Saybrook | Morgan | Old Saybrook High School - Old Saybrook Tennis Courts |
| WED 4/22 | 4:00 PM | League | Westbrook | North Branford | Westbrook High School - Westbrook HS / MS Tennis Courts |
| THU 4/23 | 3:30 PM | League | Avon | Maloney | Avon Middle School - Thompson Brook School |
| THU 4/23 | 3:45 PM | League | Coginchaug | Haddam Killingworth | Coginchaug Regional High School - Tennis Courts @ CRHS |
| THU 4/23 | 3:45 PM | League | Shepaug Valley | Nonnewaug | Shepaug Valley High School - Shepaug Valley Tennis Courts |
| THU 4/23 | 3:45 PM | League | Southington | Glastonbury | Southington High School - Tennis Courts |
| THU 4/23 | 3:45 PM | League | Mercy | Cheshire | Wesleyan University - Tennis Courts |
| THU 4/23 | 3:45 PM | League | West Haven | Lyman Hall | West Haven High School - West Haven Tennis Courts |
| THU 4/23 | 4:00 PM | League | Danbury | Ridgefield | Danbury High School - DHS Tennis Courts |
| THU 4/23 | 4:00 PM | League | Fairfield Warde | Darien | Fairfield Warde High School - Blake Courts |
| THU 4/23 | 4:00 PM | League | Norwalk | Trumbull | Grassroots Tennis and Education - Grassroots Tennis Courts |
| THU 4/23 | 4:00 PM | League | Greenwich | Stamford | Greenwich High School - GHS Tennis Courts |
| THU 4/23 | 4:00 PM | League | St. Joseph | Wilton | St. Joseph High School - Tennis Courts |
| THU 4/23 | 4:00 PM | League | Staples | Fairfield Ludlowe | Staples High School - Staples Tennis Courts |
| THU 4/23 | 4:00 PM | League | Westhill | New Canaan | Westhill High School - Westhill Tennis Courts |
| THU 4/23 | 5:00 PM | League | Bridgeport Central | Brien McMahon | Bridgeport Central High School - Central High School Tennis Courts |
| FRI 4/24 | 12:01 AM | League | Prince Tech | Platt | TBA - TBA |
| FRI 4/24 | 2:00 PM | League | Abbott Tech | Wilcox Tech | WCSU O'Neill Center - Tennis Courts |
| FRI 4/24 | 3:30 PM | League | Seymour | Wilby | Seymour High School - Tennis |
| FRI 4/24 | 3:30 PM | League | Wolcott | Naugatuck | Wolcott High School - WHS Tennis Courts |
| FRI 4/24 | 3:45 PM | League | Bristol Central | E.O. Smith | Bristol Central High School - Tennis Courts |
| FRI 4/24 | 3:45 PM | League | Bloomfield | East Catholic | Carmen Arace Middle School - Tennis Courts |
| FRI 4/24 | 3:45 PM | League | East Haven | Sheehan | East Haven High School - Tennis Court |
| FRI 4/24 | 3:45 PM | League | Farmington | Hall | Farmington High School - Large Gymnasium |
| FRI 4/24 | 3:45 PM | League | Kennedy | Torrington | John F. Kennedy High School - Chase Park |
| FRI 4/24 | 3:45 PM | League | Killingly | St. Bernard | Killingly High School - Tennis Courts |
| FRI 4/24 | 3:45 PM | League | Manchester | Simsbury | Manchester High School - Manchester |
| FRI 4/24 | 3:45 PM | League | Middletown | Lewis Mills | Middletown Tennis Courts - Beman Tennis Courts |
| FRI 4/24 | 3:45 PM | League | Montville | New London | Montville High School - Tennis Courts |
| FRI 4/24 | 3:45 PM | League | New Britain | Bristol Eastern | New Britain High School - tennis courts |
| FRI 4/24 | 3:45 PM | League | Newington | South Windsor | Newington High School - Tennis Courts |
| FRI 4/24 | 3:45 PM | League | North Branford | Lyme-Old Lyme | North Branford - NBHS Tennis Courts |
| FRI 4/24 | 3:45 PM | League | Northwestern | Gilbert | Northwestern Regional H.S. - Tennis Courts |
| FRI 4/24 | 3:45 PM | League | Plainville | Enfield | Plainville High School - PHS Tennis Courts |
| FRI 4/24 | 3:45 PM | League | Platt | Conard | Platt High School - Tennis Court |
| FRI 4/24 | 3:45 PM | League | NFA | Woodstock Academy | Rec Fields - Armstrong Tennis Courts |
| FRI 4/24 | 3:45 PM | League | RHAM | East Hartford | RHAM High School - Tennis Courts |
| FRI 4/24 | 3:45 PM | League | Rockville | Ellington | Rockville High School - RHS Tennis Courts |
| FRI 4/24 | 3:45 PM | League | Stonington | Fitch | Stonington High School - SHS Tennis Courts |
| FRI 4/24 | 3:45 PM | League | Watertown | St. Paul Catholic | TBA - TBA |
| FRI 4/24 | 3:45 PM | League | Northwest Catholic | Tolland | University of Saint Joseph - West Hartford - Tennis Courts |
| FRI 4/24 | 3:45 PM | League | Valley Regional | Cromwell | Valley Regional High School - Tennis Courts |
| FRI 4/24 | 3:45 PM | League | Notre Dame Prep | Stratford | Veteran's Park - Bridgeport - Tennis Courts |
| FRI 4/24 | 3:45 PM | League | Grasso Tech | Norwich Tech | Washington Park - Washington Park Tennis Courts |
| FRI 4/24 | 3:45 PM | League | Waterford | East Lyme | Waterford High School - Tennis Courts - WHS |
| FRI 4/24 | 3:45 PM | League | Wethersfield | Berlin | Wethersfield High School - Tennis Courts |
| FRI 4/24 | 3:45 PM | League | Windham | Lyman Memorial | Windham High School - WHS Courts |
| FRI 4/24 | 3:45 PM | League | Windsor | Rocky Hill | Windsor High School - Tennis Courts |
| FRI 4/24 | 4:00 PM | League | East Hampton | Old Saybrook | East Hampton High School - Tennis Courts |
| FRI 4/24 | 4:00 PM | League | Granby Memorial | Coventry | Granby Memorial High School - Granby |
| FRI 4/24 | 4:00 PM | League | Lakeview | Housatonic Regional | Lakeview Regional High School - Tennis Courts |
| SAT 4/25 | 11:00 AM | Non-League | Branford | Stonington | Branford High School - Tennis Courts |
| SAT 4/25 | 2:00 PM | League | Foran | Guilford | Foran High School - Foran Tennis Courts |
| MON 4/27 | 12:01 AM | League | Woodstock Academy | East Lyme | Pomfret School - Field House |
| MON 4/27 | 12:01 AM | League | Prince Tech | Wilcox Tech | TBA - TBA |
| MON 4/27 | 2:00 PM | League | Abbott Tech | Norwich Tech | WCSU O'Neill Center - Tennis Courts |
| MON 4/27 | 3:30 PM | League | Avon | Berlin | Avon Middle School - Thompson Brook School |
| MON 4/27 | 3:30 PM | League | Wolcott | Kennedy | Wolcott High School - WHS Tennis Courts |
| MON 4/27 | 3:30 PM | League | Woodland | Seymour | Woodland High School - Tennis Courts |
| MON 4/27 | 3:45 PM | League | Bethel | Weston | Bethel High School - BHS Tennis Courts |
| MON 4/27 | 3:45 PM | League | Branford | Sheehan | Branford High School - Tennis Courts |
| MON 4/27 | 3:45 PM | League | Bristol Central | Middletown | Bristol Central High School - Tennis Courts |
| MON 4/27 | 3:45 PM | League | Bristol Eastern | Bloomfield | Bristol Eastern High School - Tennis Court |
| MON 4/27 | 3:45 PM | League | Brookfield | Pomperaug | Brookfield High School - BHS Tennis Courts |
| MON 4/27 | 3:45 PM | League | Bunnell | Bassick | Bunnell HS - Bunnell Tennis Courts |
| MON 4/27 | 3:45 PM | League | Cheshire | Daniel Hand | Cheshire High School - Tennis Courts |
| MON 4/27 | 3:45 PM | League | Coginchaug | Lyme-Old Lyme | Coginchaug Regional High School - Tennis Courts @ CRHS |
| MON 4/27 | 3:45 PM | League | Conard | Windsor | Conard High School - Tennis Courts |
| MON 4/27 | 3:45 PM | League | East Granby | Ellington | East Granby High School - EGHS Tennis Courts |
| MON 4/27 | 3:45 PM | League | East Haven | Foran | East Haven High School - Tennis Court |
| MON 4/27 | 3:45 PM | League | Fitch | New London | Fitch High School - Main Tennis Courts |
| MON 4/27 | 3:45 PM | League | Hall | Southington | Hall High School - Tennis Courts |
| MON 4/27 | 3:45 PM | League | Hamden | West Haven | Hamden Middle School - Tennis Courts |
| MON 4/27 | 3:45 PM | League | Joel Barlow | New Milford | Joel Barlow High School - Tennis Courts |
| MON 4/27 | 3:45 PM | League | Ledyard | Killingly | Ledyard High School - Tennis Courts |
| MON 4/27 | 3:45 PM | League | Montville | Stonington | Montville High School - Tennis Courts |
| MON 4/27 | 3:45 PM | League | Naugatuck | Wilby | Naugatuck High School - Tennis Courts |
| MON 4/27 | 3:45 PM | League | North Branford | Portland | North Branford - NBHS Tennis Courts |
| MON 4/27 | 3:45 PM | League | North Haven | Jonathan Law | North Haven Athletic Complex - Tennis Courts |
| MON 4/27 | 3:45 PM | League | Northwestern | Housatonic Regional | Northwestern Regional H.S. - Tennis Courts |
| MON 4/27 | 3:45 PM | League | Stratford | Notre Dame Prep | Penders Field - Tennis Courts |
| MON 4/27 | 3:45 PM | League | Plainville | Northwest Catholic | Plainville High School - PHS Tennis Courts |
| MON 4/27 | 3:45 PM | League | Immaculate | Newtown | Rogers Park - Tennis Courts |
| MON 4/27 | 3:45 PM | League | Shelton | Amity | Shelton High School - Tennis Courts |
| MON 4/27 | 3:45 PM | League | St. Bernard | NFA | St. Bernard School - Tennis Courts |
| MON 4/27 | 3:45 PM | League | Watertown | Torrington | TBA - TBA |
| MON 4/27 | 3:45 PM | League | Thomaston | Lakeview | Thomaston Nystrom Park - Nystroms Park courts |
| MON 4/27 | 3:45 PM | League | Valley Regional | Westbrook | Valley Regional High School - Tennis Courts |
| MON 4/27 | 3:45 PM | League | Gilbert | Nonnewaug | Walker Field - Tennis Courts |
| MON 4/27 | 3:45 PM | League | Grasso Tech | Platt Tech | Washington Park - Washington Park Tennis Courts |
| MON 4/27 | 3:45 PM | League | Masuk | New Fairfield | Wolfe Park - Tennis Courts |
| MON 4/27 | 4:00 PM | League | Coventry | Suffield | Coventry High School - tennis courts |
| MON 4/27 | 4:00 PM | League | Cromwell | Morgan | Cromwell Middle School - Waterous Park Tennis Courts |
| MON 4/27 | 4:00 PM | League | Danbury | Greenwich | Danbury High School - DHS Tennis Courts |
| MON 4/27 | 4:00 PM | League | Darien | New Canaan | Darien High School - DHS Tennis Courts |
| MON 4/27 | 4:00 PM | League | Fairfield Warde | Fairfield Ludlowe | Fairfield Warde High School - Blake Courts |
| MON 4/27 | 4:00 PM | League | Norwalk | Brien McMahon | Grassroots Tennis and Education - Grassroots Tennis Courts |
| MON 4/27 | 4:00 PM | League | Lyman Memorial | Windham | Lyman Memorial High School - Tennis Courts |
| MON 4/27 | 4:00 PM | League | Newington | Maloney | Newington High School - Tennis Courts |
| MON 4/27 | 4:00 PM | League | Old Saybrook | Haddam Killingworth | Old Saybrook High School - Old Saybrook Tennis Courts |
| MON 4/27 | 4:00 PM | League | Rockville | Canton | Rockville High School - RHS Tennis Courts |
| MON 4/27 | 4:00 PM | League | St. Joseph | Trumbull | St. Joseph High School - Tennis Courts |
| MON 4/27 | 4:00 PM | League | Staples | Bridgeport Central | Staples High School - Staples Tennis Courts |
| MON 4/27 | 4:00 PM | League | Westhill | Stamford | Westhill High School - Westhill Tennis Courts |
| MON 4/27 | 4:00 PM | League | Wilton | Ridgefield | Wilton High School - Allen Meadow |
| TUE 4/28 | 3:30 PM | Non-League | Platt Tech | Foran | Eisenhower Park - Eisenhower Park |
| TUE 4/28 | 3:45 PM | League | Lyman Hall | Lauralton Hall | Doolittle Park - Doolittle Tennis Courts |
| TUE 4/28 | 3:45 PM | League | Farmington | East Hartford | Farmington High School - Large Gymnasium |
| TUE 4/28 | 3:45 PM | League | Glastonbury | Wethersfield | Glastonbury High School - Tennis Courts |
| TUE 4/28 | 3:45 PM | League | Lewis Mills | Platt | Lewis Mills High School - Tennis Courts |
| TUE 4/28 | 3:45 PM | League | Manchester | East Catholic | Manchester High School - Manchester |
| TUE 4/28 | 3:45 PM | League | Newington | RHAM | Newington High School - Tennis Courts |
| TUE 4/28 | 3:45 PM | League | Simsbury | New Britain | Simsbury High School - Tennis Courts |
| TUE 4/28 | 3:45 PM | League | South Windsor | Maloney | South Windsor High School - Wapping Tennis Courts |
| TUE 4/28 | 3:45 PM | League | Tolland | Rocky Hill | Tolland High School - Tennis Courts |
| TUE 4/28 | 4:00 PM | League | Darien | Danbury | Darien High School - DHS Tennis Courts |
| TUE 4/28 | 4:00 PM | League | Fairfield Ludlowe | Stamford | Fairfield Ludlowe High School - Tennis Courts |
| TUE 4/28 | 4:00 PM | League | Fairfield Warde | Norwalk | Fairfield Warde High School - Blake Courts |
| TUE 4/28 | 4:00 PM | League | New Canaan | Bridgeport Central | New Canaan HS - NCHS Tennis Courts |
| TUE 4/28 | 4:00 PM | League | Ridgefield | Greenwich | Ridgefield High School - RHS Tennis Courts |
| TUE 4/28 | 4:00 PM | League | St. Joseph | Brien McMahon | St. Joseph High School - Tennis Courts |
| TUE 4/28 | 4:00 PM | League | Trumbull | Staples | Trumbull High School - Tennis Courts |
| TUE 4/28 | 4:00 PM | League | Wilton | Westhill | Wilton High School - Allen Meadow |
| TUE 4/28 | 5:00 AM | League | Enfield | E.O. Smith | Enfield High School - EHS TENNIS COURTS |
| WED 4/29 | 12:01 AM | League | Woodstock Academy | Lyman Memorial | Pomfret School - Field House |
| WED 4/29 | 12:01 AM | League | Prince Tech | Abbott Tech | TBA - TBA |
| WED 4/29 | 3:30 PM | League | New Fairfield | Weston | New Fairfield High School - Tennis Courts |
| WED 4/29 | 3:30 PM | League | Torrington | Ansonia | Torrington High School - Tennis Courts |
| WED 4/29 | 3:30 PM | League | Woodland | Wolcott | Woodland High School - Tennis Courts |
| WED 4/29 | 3:45 PM | League | Amity | East Haven | Amity Regional High School - Tennis Courts |
| WED 4/29 | 3:45 PM | League | Bolton | Coventry | Bolton High School - BHS Tennis Courts |
| WED 4/29 | 3:45 PM | League | Bloomfield | Lewis Mills | Carmen Arace Middle School - Tennis Courts |
| WED 4/29 | 3:45 PM | League | Coginchaug | Westbrook | Coginchaug Regional High School - Tennis Courts @ CRHS |
| WED 4/29 | 3:45 PM | League | Conard | Tolland | Conard High School - Tennis Courts |
| WED 4/29 | 3:45 PM | League | East Granby | Granby Memorial | East Granby High School - EGHS Tennis Courts |
| WED 4/29 | 3:45 PM | League | East Hartford | Wethersfield | East Hartford High School - Tennis Courts |
| WED 4/29 | 3:45 PM | League | East Lyme | Fitch | East Lyme High School - Tennis Courts |
| WED 4/29 | 3:45 PM | League | Foran | Lyman Hall | Foran High School - Foran Tennis Courts |
| WED 4/29 | 3:45 PM | League | Glastonbury | South Windsor | Glastonbury High School - Tennis Courts |
| WED 4/29 | 3:45 PM | League | Guilford | Career Magnet | Guilford High School - GHS Tennis Courts |
| WED 4/29 | 3:45 PM | League | Joel Barlow | Brookfield | Joel Barlow High School - Tennis Courts |
| WED 4/29 | 3:45 PM | League | Ledyard | NFA | Ledyard High School - Tennis Courts |
| WED 4/29 | 3:45 PM | League | Lyme-Old Lyme | Portland | Lyme-Old Lyme High School - Tennis Courts |
| WED 4/29 | 3:45 PM | League | Maloney | Farmington | Maloney High School - Tennis Courts |
| WED 4/29 | 3:45 PM | League | Naugatuck | Watertown | Naugatuck High School - Tennis Courts |
| WED 4/29 | 3:45 PM | League | New Britain | East Catholic | New Britain High School - tennis courts |
| WED 4/29 | 3:45 PM | League | Newtown | Pomperaug | Newtown High School - NHS Tennis Courts |
| WED 4/29 | 3:45 PM | League | North Haven | Hamden | North Haven Athletic Complex - Tennis Courts |
| WED 4/29 | 3:45 PM | League | Northwestern | Lakeview | Northwestern Regional H.S. - Tennis Courts |
| WED 4/29 | 3:45 PM | League | Rocky Hill | Manchester | Rocky Hill High School - Tennis Courts |
| WED 4/29 | 3:45 PM | League | Immaculate | Bunnell | Rogers Park - Tennis Courts |
| WED 4/29 | 3:45 PM | League | Sheehan | Cheshire | Sheehan High School - Sheehan HS Tennis Courts |
| WED 4/29 | 3:45 PM | League | Shelton | Sacred Heart Academy | Shelton High School - Tennis Courts |
| WED 4/29 | 3:45 PM | League | Shepaug Valley | Housatonic Regional | Shepaug Valley High School - Shepaug Valley Tennis Courts |
| WED 4/29 | 3:45 PM | League | Simsbury | E.O. Smith | Simsbury High School - Tennis Courts |
| WED 4/29 | 3:45 PM | League | Thomaston | Gilbert | Thomaston Nystrom Park - Nystroms Park courts |
| WED 4/29 | 3:45 PM | League | Valley Regional | Haddam Killingworth | Valley Regional High School - Tennis Courts |
| WED 4/29 | 3:45 PM | League | Waterford | Stonington | Waterford High School - Tennis Courts - WHS |
| WED 4/29 | 3:45 PM | League | Wilby | Kennedy | Wilby High School - Dave Krill Tennis Courts at WHS |
| WED 4/29 | 3:45 PM | League | Windham | St. Bernard | Windham High School - WHS Courts |
| WED 4/29 | 3:45 PM | League | Masuk | Notre Dame Prep | Wolfe Park - Tennis Courts |
| WED 4/29 | 4:00 PM | League | Cromwell | Old Saybrook | Cromwell Middle School - Waterous Park Tennis Courts |
| WED 4/29 | 4:00 PM | League | Morgan | East Hampton | Morgan School - Tennis Courts |
| WED 4/29 | 4:00 PM | League | New London | Montville | New London High School - NLHS Tennis Courts |
| WED 4/29 | 5:00 AM | League | Enfield | Middletown | Enfield High School - EHS TENNIS COURTS |
| THU 4/30 | 3:45 PM | League | Berlin | Hall | Berlin High School - Tennis Courts |
| THU 4/30 | 3:45 PM | League | Bristol Central | Windsor | Bristol Central High School - Tennis Courts |
| THU 4/30 | 3:45 PM | League | Jonathan Law | West Haven | Jonathan Law High School - Tennis Courts |
| THU 4/30 | 3:45 PM | League | New Fairfield | Bunnell | New Fairfield High School - Tennis Courts |
| THU 4/30 | 3:45 PM | League | North Haven | East Haven | North Haven Athletic Complex - Tennis Courts |
| THU 4/30 | 3:45 PM | League | Platt | Plainville | Platt High School - Tennis Court |
| THU 4/30 | 3:45 PM | League | RHAM | Avon | RHAM High School - Tennis Courts |
| THU 4/30 | 3:45 PM | League | Southington | Newington | Southington High School - Tennis Courts |
| THU 4/30 | 3:45 PM | League | Northwest Catholic | Bristol Eastern | University of Saint Joseph - West Hartford - Tennis Courts |
| THU 4/30 | 3:45 PM | League | Masuk | Immaculate | Wolfe Park - Tennis Courts |
| THU 4/30 | 4:00 PM | League | Danbury | Staples | Danbury High School - DHS Tennis Courts |
| THU 4/30 | 4:00 PM | League | Darien | Fairfield Ludlowe | Darien High School - DHS Tennis Courts |
| THU 4/30 | 4:00 PM | League | Fairfield Warde | Stamford | Fairfield Warde High School - Blake Courts |
| THU 4/30 | 4:00 PM | League | Granby Memorial | Canton | Granby Memorial High School - Tennis Courts |
| THU 4/30 | 4:00 PM | League | Norwalk | Greenwich | Grassroots Tennis and Education - Grassroots Tennis Courts |
| THU 4/30 | 4:00 PM | League | New Canaan | St. Joseph | New Canaan HS - NCHS Tennis Courts |
| THU 4/30 | 4:00 PM | League | Trumbull | Ridgefield | Trumbull High School - Tennis Courts |
| THU 4/30 | 4:00 PM | League | Westhill | Bridgeport Central | Westhill High School - Westhill Tennis Courts |
| THU 4/30 | 4:00 PM | League | Wilton | Brien McMahon | Wilton High School - Allen Meadow |
| THU 4/30 | 4:00 PM | Non-League | Lakeview | Mercy | Lakeview Regional High School - Tennis Courts |
| FRI 5/1 | 2:00 PM | League | Abbott Tech | Grasso Tech | WCSU O'Neill Center - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Berlin | Plainville | Berlin High School - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Bethel | Joel Barlow | Bethel High School - BHS Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Bolton | Ellington | Bolton High School - BHS Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Bristol Central | Lewis Mills | Bristol Central High School - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Bristol Eastern | Farmington | Bristol Eastern High School - Tennis Court |
| FRI 5/1 | 3:45 PM | League | Bloomfield | Hall | Carmen Arace Middle School - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | E.O. Smith | Windsor | E.O. Smith High School - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | East Lyme | Montville | East Lyme High School - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Fitch | St. Bernard | Fitch High School - Main Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Glastonbury | East Hartford | Glastonbury High School - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Haddam Killingworth | East Hampton | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Hamden | Shelton | Hamden Middle School - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Housatonic Regional | Nonnewaug | Housatonic Valley Regional High - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Ledyard | Woodstock Academy | Ledyard High School - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Middletown | Platt | Middletown Tennis Courts - Beman Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Newington | Maloney | Newington High School - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Northwestern | Thomaston | Northwestern Regional H.S. - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Pomperaug | Stratford | Pomperaug High School - PHS Tennis Courts |
| FRI 5/1 | 3:45 PM | League | NFA | Killingly | Rec Fields - Armstrong Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Rocky Hill | Southington | Rocky Hill High School - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Sheehan | Lyman Hall | Sheehan High School - Sheehan HS Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Simsbury | Conard | Simsbury High School - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | South Windsor | Tolland | South Windsor High School - Wapping Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Northwest Catholic | Avon | University of Saint Joseph - West Hartford - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Notre Dame Prep | Newtown | Veteran's Park - Bridgeport - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Gilbert | Shepaug Valley | Walker Field - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Mercy | Amity | Wesleyan University - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | West Haven | Sacred Heart Academy | West Haven High School - West Haven Tennis Courts |
| FRI 5/1 | 3:45 PM | League | Wethersfield | New Britain | Wethersfield High School - Tennis Courts |
| FRI 5/1 | 3:45 PM | League | East Catholic | Manchester | Wickham Park - Wickham Park |
| FRI 5/1 | 3:45 PM | League | Windham | Waterford | Windham High School - WHS Courts |
| FRI 5/1 | 3:45 PM | League | Windsor Locks | Suffield | Windsor Locks High School - Tennis Court |
| FRI 5/1 | 4:00 PM | League | Lyme-Old Lyme | Old Saybrook | Lyme-Old Lyme High School - Tennis Courts |
| FRI 5/1 | 4:00 PM | League | New London | Windham | New London High School - NLHS Tennis Courts |
| FRI 5/1 | 4:00 PM | League | Rockville | East Granby | Rockville High School - RHS Tennis Courts |
| FRI 5/1 | 4:00 PM | League | Stonington | Lyman Memorial | Stonington High School - SHS Tennis Courts |
| FRI 5/1 | 4:00 PM | League | Westbrook | Morgan | Westbrook High School - Westbrook HS / MS Tennis Courts |
| FRI 5/1 | 5:00 AM | League | Enfield | RHAM | Enfield High School - EHS TENNIS COURTS |
| SAT 5/2 | 12:00 PM | League | Stonington | Granby Memorial | Stonington High School - SHS Tennis Courts |
| MON 5/4 | 2:00 PM | League | Abbott Tech | Platt Tech | WCSU O'Neill Center - Tennis Courts |
| MON 5/4 | 3:30 PM | League | Avon | Bloomfield | Avon Middle School - Thompson Brook School |
| MON 5/4 | 3:30 PM | League | Seymour | Torrington | Seymour High School - Tennis |
| MON 5/4 | 3:30 PM | League | Wolcott | Holy Cross | Wolcott High School - WHS Tennis Courts |
| MON 5/4 | 3:45 PM | League | Amity | Hamden | Amity Regional High School - Tennis Courts |
| MON 5/4 | 3:45 PM | League | Brookfield | Masuk | Brookfield High School - BHS Tennis Courts |
| MON 5/4 | 3:45 PM | League | Conard | Northwest Catholic | Conard High School - Tennis Courts |
| MON 5/4 | 3:45 PM | League | Lyman Hall | Cheshire | Doolittle Park - Doolittle Tennis Courts |
| MON 5/4 | 3:45 PM | League | E.O. Smith | Enfield | E.O. Smith High School - Tennis Courts |
| MON 5/4 | 3:45 PM | League | East Lyme | Ledyard | East Lyme High School - Tennis Courts |
| MON 5/4 | 3:45 PM | League | Farmington | Bristol Central | Farmington High School - Large Gymnasium |
| MON 5/4 | 3:45 PM | League | Fitch | Woodstock Academy | Fitch High School - Main Tennis Courts |
| MON 5/4 | 3:45 PM | League | Guilford | Branford | Guilford High School - GHS Tennis Courts |
| MON 5/4 | 3:45 PM | League | Hall | Bristol Eastern | Hall High School - Tennis Courts |
| MON 5/4 | 3:45 PM | League | Killingly | Waterford | Killingly High School - Tennis Courts |
| MON 5/4 | 3:45 PM | League | Lewis Mills | Simsbury | Lewis Mills High School - Tennis Courts |
| MON 5/4 | 3:45 PM | League | Maloney | Rocky Hill | Maloney High School - Tennis Courts |
| MON 5/4 | 3:45 PM | League | Manchester | Windsor | Manchester High School - Manchester |
| MON 5/4 | 3:45 PM | League | Naugatuck | St. Paul Catholic | Naugatuck High School - Tennis Courts |
| MON 5/4 | 3:45 PM | League | New Fairfield | Notre Dame Prep | New Fairfield High School - Tennis Courts |
| MON 5/4 | 3:45 PM | League | Newington | New Britain | Newington High School - Tennis Courts |
| MON 5/4 | 3:45 PM | League | North Haven | Shelton | North Haven Athletic Complex - Tennis Courts |
| MON 5/4 | 3:45 PM | League | Norwich Tech | Prince Tech | Norwich Technical High School - NTHS Outdoor Athletic Complex |
| MON 5/4 | 3:45 PM | League | Stratford | Newtown | Penders Field - Tennis Courts |
| MON 5/4 | 3:45 PM | League | Plainville | Wethersfield | Plainville High School - PHS Tennis Courts |
| MON 5/4 | 3:45 PM | League | Platt | Berlin | Platt High School - Tennis Court |
| MON 5/4 | 3:45 PM | League | NFA | Lyman Memorial | Rec Fields - Armstrong Tennis Courts |
| MON 5/4 | 3:45 PM | League | RHAM | Glastonbury | RHAM High School - Tennis Courts |
| MON 5/4 | 3:45 PM | League | Immaculate | Bethel | Rogers Park - Tennis Courts |
| MON 5/4 | 3:45 PM | League | East Hartford | South Windsor | South Windsor High School - Wapping Tennis Courts |
| MON 5/4 | 3:45 PM | League | Southington | Middletown | Southington High School - Tennis Courts |
| MON 5/4 | 3:45 PM | League | Watertown | Woodland | TBA - TBA |
| MON 5/4 | 3:45 PM | League | Thomaston | Nonnewaug | Thomaston Nystrom Park - Nystroms Park courts |
| MON 5/4 | 3:45 PM | League | Tolland | East Catholic | Tolland High School - Tennis Courts |
| MON 5/4 | 3:45 PM | League | Gilbert | Housatonic Regional | Walker Field - Tennis Courts |
| MON 5/4 | 3:45 PM | League | West Haven | Mercy | West Haven High School - West Haven Tennis Courts |
| MON 5/4 | 3:45 PM | League | Westbrook | Haddam Killingworth | Westbrook High School - Westbrook HS / MS Tennis Courts |
| MON 5/4 | 3:45 PM | League | Weston | New Milford | Weston High School - WHS Tennis Courts |
| MON 5/4 | 3:45 PM | League | Windsor Locks | East Granby | Windsor Locks High School - Tennis Court |
| MON 5/4 | 4:00 PM | League | Brien McMahon | Fairfield Warde | Brien McMahon High School - Tennis Courts |
| MON 5/4 | 4:00 PM | League | East Hampton | North Branford | East Hampton High School - Tennis Courts |
| MON 5/4 | 4:00 PM | League | Ellington | Coventry | Ellington High School - Tennis Courts |
| MON 5/4 | 4:00 PM | League | Fairfield Ludlowe | Wilton | Fairfield Ludlowe High School - Tennis Courts |
| MON 5/4 | 4:00 PM | League | Granby Memorial | Rockville | Granby Memorial High School - Tennis Courts |
| MON 5/4 | 4:00 PM | League | Greenwich | Westhill | Greenwich High School - GHS Tennis Courts |
| MON 5/4 | 4:00 PM | League | Lakeview | Shepaug Valley | Lakeview Regional High School - Tennis Courts |
| MON 5/4 | 4:00 PM | League | Lyme-Old Lyme | Cromwell | Lyme-Old Lyme High School - Tennis Courts |
| MON 5/4 | 4:00 PM | League | Morgan | Portland | Morgan School - Tennis Courts |
| MON 5/4 | 4:00 PM | League | New Canaan | Trumbull | New Canaan HS - NCHS Tennis Courts |
| MON 5/4 | 4:00 PM | League | Old Saybrook | Valley Regional | Old Saybrook High School - Old Saybrook Tennis Courts |
| MON 5/4 | 4:00 PM | League | Ridgefield | Darien | Ridgefield High School - RHS Tennis Courts |
| MON 5/4 | 4:00 PM | League | Stamford | Norwalk | Stamford High School - SHS Tennis Courts |
| MON 5/4 | 4:00 PM | League | Staples | St. Joseph | Staples High School - Staples Tennis Courts |
| MON 5/4 | 5:00 PM | League | Bridgeport Central | Danbury | Bridgeport Central High School - Central High School Tennis Courts |
| TUE 5/5 | 3:30 PM | Non-League | Pomperaug | Nonnewaug | Pomperaug High School - PHS Tennis Courts |
| TUE 5/5 | 3:45 PM | League | Montville | St. Bernard | Montville High School - Tennis Courts |
| TUE 5/5 | 4:00 PM | League | Brien McMahon | Darien | Brien McMahon High School - Tennis Courts |
| TUE 5/5 | 4:00 PM | League | Fairfield Ludlowe | Trumbull | Fairfield Ludlowe High School - Tennis Courts |
| TUE 5/5 | 4:00 PM | League | Greenwich | Fairfield Warde | Greenwich High School - GHS Tennis Courts |
| TUE 5/5 | 4:00 PM | League | Lyman Memorial | Ledyard | Lyman Memorial High School - Tennis Courts |
| TUE 5/5 | 4:00 PM | League | Ridgefield | New Canaan | Ridgefield High School - RHS Tennis Courts |
| TUE 5/5 | 4:00 PM | League | St. Joseph | Danbury | St. Joseph High School - Tennis Courts |
| TUE 5/5 | 4:00 PM | League | Stamford | Wilton | Stamford High School - SHS Tennis Courts |
| TUE 5/5 | 4:00 PM | League | Staples | Westhill | Staples High School - Staples Tennis Courts |
| TUE 5/5 | 5:00 PM | League | Bridgeport Central | Norwalk | Bridgeport Central High School - Central High School Tennis Courts |
| WED 5/6 | 3:30 PM | League | Waterford | Fitch | Waterford High School - Tennis Courts - WHS |
| WED 5/6 | 3:30 PM | League | Wolcott | Seymour | Wolcott High School - WHS Tennis Courts |
| WED 5/6 | 3:30 PM | League | Woodland | Crosby | Woodland High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Bethel | Bunnell | Bethel High School - BHS Tennis Courts |
| WED 5/6 | 3:45 PM | League | Bolton | East Granby | Bolton High School - BHS Tennis Courts |
| WED 5/6 | 3:45 PM | League | Bloomfield | Bristol Eastern | Carmen Arace Middle School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Cheshire | Lauralton Hall | Cheshire High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Conard | Lewis Mills | Conard High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | East Hartford | RHAM | East Hartford High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Platt Tech | Norwich Tech | Eisenhower Park - Eisenhower Park |
| WED 5/6 | 3:45 PM | League | Foran | Sacred Heart Academy | Foran High School - Foran Tennis Courts |
| WED 5/6 | 3:45 PM | League | Glastonbury | Tolland | Glastonbury High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Haddam Killingworth | Coginchaug | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| WED 5/6 | 3:45 PM | League | Hall | Farmington | Hall High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Hamden | Branford | Hamden Middle School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Joel Barlow | Bassick | Joel Barlow High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Jonathan Law | Mercy | Jonathan Law High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Killingly | New London | Killingly High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Manchester | E.O. Smith | Manchester High School - Manchester |
| WED 5/6 | 3:45 PM | League | Naugatuck | Torrington | Naugatuck High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | New Britain | Plainville | New Britain High School - tennis courts |
| WED 5/6 | 3:45 PM | League | New Fairfield | Stratford | New Fairfield High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Newington | Berlin | Newington High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | North Haven | Amity | North Haven Athletic Complex - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Northwestern | Nonnewaug | Northwestern Regional H.S. - Tennis Courts |
| WED 5/6 | 3:45 PM | League | NFA | Montville | Rec Fields - Armstrong Tennis Courts |
| WED 5/6 | 3:45 PM | League | Rocky Hill | Middletown | Rocky Hill High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Immaculate | Brookfield | Rogers Park - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Sheehan | West Haven | Sheehan High School - Sheehan HS Tennis Courts |
| WED 5/6 | 3:45 PM | League | Shelton | Lyman Hall | Shelton High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Simsbury | Avon | Simsbury High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | South Windsor | Enfield | South Windsor High School - Wapping Tennis Courts |
| WED 5/6 | 3:45 PM | League | Southington | Platt | Southington High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Stonington | East Lyme | Stonington High School - SHS Tennis Courts |
| WED 5/6 | 3:45 PM | League | Watertown | Ansonia | TBA - TBA |
| WED 5/6 | 3:45 PM | League | Thomaston | Shepaug Valley | Thomaston Nystrom Park - Nystroms Park courts |
| WED 5/6 | 3:45 PM | League | Northwest Catholic | Bristol Central | University of Saint Joseph - West Hartford - Tennis Courts |
| WED 5/6 | 3:45 PM | League | Wethersfield | Maloney | Wethersfield High School - Tennis Courts |
| WED 5/6 | 3:45 PM | League | East Catholic | Windsor | Wickham Park - Wickham Park |
| WED 5/6 | 3:45 PM | League | Windham | Woodstock Academy | Windham High School - WHS Courts |
| WED 5/6 | 3:45 PM | League | Masuk | Weston | Wolfe Park - Tennis Courts |
| WED 5/6 | 4:00 PM | League | Coventry | Rockville | Coventry High School - tennis courts |
| WED 5/6 | 4:00 PM | League | Cromwell | North Branford | Cromwell Middle School - Waterous Park Tennis Courts |
| WED 5/6 | 4:00 PM | League | East Hampton | Lyme-Old Lyme | East Hampton High School - Tennis Courts |
| WED 5/6 | 4:00 PM | League | Ellington | Canton | Ellington High School - Tennis Courts |
| WED 5/6 | 4:00 PM | League | Lakeview | Gilbert | Lakeview Regional High School - Tennis Courts |
| WED 5/6 | 4:00 PM | League | Old Saybrook | Westbrook | Old Saybrook High School - Old Saybrook Tennis Courts |
| THU 5/7 | 3:45 PM | League | East Haven | Lyman Hall | East Haven High School - Tennis Court |
| THU 5/7 | 3:45 PM | League | East Lyme | Waterford | East Lyme High School - Tennis Courts |
| THU 5/7 | 3:45 PM | League | Jonathan Law | Foran | Jonathan Law High School - Tennis Courts |
| THU 5/7 | 3:45 PM | League | Ledyard | Fitch | Ledyard High School - Tennis Courts |
| THU 5/7 | 3:45 PM | Non-League | Guilford | Branford | Guilford High School - GHS Tennis Courts |
| THU 5/7 | 4:00 PM | League | Brien McMahon | Greenwich | Brien McMahon High School - Tennis Courts |
| THU 5/7 | 4:00 PM | League | Darien | Norwalk | Darien High School - DHS Tennis Courts |
| THU 5/7 | 4:00 PM | League | Fairfield Ludlowe | Bridgeport Central | Fairfield Ludlowe High School - Tennis Courts |
| THU 5/7 | 4:00 PM | League | Morgan | Cromwell | Morgan School - Tennis Courts |
| THU 5/7 | 4:00 PM | League | New Canaan | Danbury | New Canaan HS - NCHS Tennis Courts |
| THU 5/7 | 4:00 PM | League | Ridgefield | Staples | Ridgefield High School - RHS Tennis Courts |
| THU 5/7 | 4:00 PM | League | St. Joseph | Stamford | St. Joseph High School - Tennis Courts |
| THU 5/7 | 4:00 PM | League | Trumbull | Westhill | Trumbull High School - Tennis Courts |
| THU 5/7 | 4:00 PM | League | Wilton | Fairfield Warde | Wilton High School - Allen Meadow |
| FRI 5/8 | 3:30 PM | League | Avon | Hall | Avon Middle School - Thompson Brook School |
| FRI 5/8 | 3:30 PM | League | Wolcott | St. Paul Catholic | Wolcott High School - WHS Tennis Courts |
| FRI 5/8 | 3:30 PM | League | Woodland | Naugatuck | Woodland High School - Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Berlin | Wethersfield | Berlin High School - Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Bolton | Windsor Locks | Bolton High School - BHS Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Bristol Central | Simsbury | Bristol Central High School - Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Bristol Eastern | Northwest Catholic | Bristol Eastern High School - Tennis Court |
| FRI 5/8 | 3:45 PM | League | Brookfield | Bethel | Brookfield High School - BHS Tennis Courts |
| FRI 5/8 | 3:45 PM | League | E.O. Smith | East Hartford | E.O. Smith High School - Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Platt Tech | Wilcox Tech | Eisenhower Park - Eisenhower Park |
| FRI 5/8 | 3:45 PM | League | Farmington | Conard | Farmington High School - Large Gymnasium |
| FRI 5/8 | 3:45 PM | League | Housatonic Regional | Northwestern | Housatonic Valley Regional High - Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Joel Barlow | Stratford | Joel Barlow High School - Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Kennedy | Seymour | John F. Kennedy High School - Chase Park |
| FRI 5/8 | 3:45 PM | League | Lewis Mills | Bloomfield | Lewis Mills High School - Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Maloney | Southington | Maloney High School - Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Middletown | Newington | Middletown Tennis Courts - Beman Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Newtown | New Milford | Newtown High School - NHS Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Nonnewaug | Gilbert | Nonnewaug High School - Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Plainville | Rocky Hill | Plainville High School - PHS Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Platt | New Britain | Platt High School - Tennis Court |
| FRI 5/8 | 3:45 PM | League | Pomperaug | Masuk | Pomperaug High School - PHS Tennis Courts |
| FRI 5/8 | 3:45 PM | League | RHAM | East Catholic | RHAM High School - Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Tolland | Manchester | Tolland High School - Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Valley Regional | Coginchaug | Valley Regional High School - Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Notre Dame Prep | Bunnell | Veteran's Park - Bridgeport - Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Grasso Tech | Abbott Tech | Washington Park - Washington Park Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Weston | Immaculate | Weston High School - WHS Tennis Courts |
| FRI 5/8 | 3:45 PM | League | Windham | Montville | Windham High School - WHS Courts |
| FRI 5/8 | 3:45 PM | League | Windsor | South Windsor | Windsor High School - Tennis Courts |
| FRI 5/8 | 4:00 PM | League | Ellington | Granby Memorial | Ellington High School - Tennis Courts |
| FRI 5/8 | 4:00 PM | League | Lakeview | Thomaston | Lakeview Regional High School - Tennis Courts |
| FRI 5/8 | 4:00 PM | League | Lyman Memorial | St. Bernard | Lyman Memorial High School - Tennis Courts |
| FRI 5/8 | 4:00 PM | League | New London | NFA | New London High School - NLHS Tennis Courts |
| FRI 5/8 | 4:00 PM | League | Portland | North Branford | Portland High School - Tennis Courts |
| FRI 5/8 | 4:00 PM | League | Rockville | Suffield | Rockville High School - RHS Tennis Courts |
| FRI 5/8 | 4:00 PM | League | Stonington | Killingly | Stonington High School - SHS Tennis Courts |
| FRI 5/8 | 5:00 AM | League | Enfield | Glastonbury | Enfield High School - EHS TENNIS COURTS |
| SAT 5/9 | 10:00 AM | League | East Haven | Wilcox Tech | East Haven High School - Tennis Court |
| SAT 5/9 | 10:00 AM | Non-League | St. Bernard | Norwich Tech | St. Bernard School - Tennis Courts |
| MON 5/11 | 12:01 AM | League | Woodstock Academy | Killingly | Pomfret School - Field House |
| MON 5/11 | 3:30 PM | League | Seymour | Watertown | Seymour High School - Tennis |
| MON 5/11 | 3:30 PM | League | Torrington | St. Paul Catholic | Torrington High School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Amity | Lauralton Hall | Amity Regional High School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Bolton | Canton | Bolton High School - BHS Tennis Courts |
| MON 5/11 | 3:45 PM | League | Branford | Career Magnet | Branford High School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Bloomfield | Farmington | Carmen Arace Middle School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Cheshire | North Haven | Cheshire High School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Conard | Bristol Eastern | Conard High School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | East Hartford | Windsor | East Hartford High School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Platt Tech | Prince Tech | Eisenhower Park - Eisenhower Park |
| MON 5/11 | 3:45 PM | League | Hall | Bristol Central | Hall High School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Hamden | East Haven | Hamden Middle School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Housatonic Regional | Thomaston | Housatonic Valley Regional High - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Kennedy | Naugatuck | John F. Kennedy High School - Chase Park |
| MON 5/11 | 3:45 PM | League | Jonathan Law | Daniel Hand | Jonathan Law High School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Ledyard | East Lyme | Ledyard High School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Lewis Mills | Avon | Lewis Mills High School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Manchester | Enfield | Manchester High School - Manchester |
| MON 5/11 | 3:45 PM | League | New Britain | Middletown | New Britain High School - tennis courts |
| MON 5/11 | 3:45 PM | League | Newington | Wethersfield | Newington High School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Newtown | Masuk | Newtown High School - NHS Tennis Courts |
| MON 5/11 | 3:45 PM | League | Nonnewaug | Lakeview | Nonnewaug High School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Norwich Tech | Abbott Tech | Norwich Technical High School - NTHS Outdoor Athletic Complex |
| MON 5/11 | 3:45 PM | League | Stratford | Bunnell | Penders Field - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Plainville | Maloney | Plainville High School - PHS Tennis Courts |
| MON 5/11 | 3:45 PM | League | Pomperaug | Immaculate | Pomperaug High School - PHS Tennis Courts |
| MON 5/11 | 3:45 PM | League | RHAM | Tolland | RHAM High School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Rocky Hill | Platt | Rocky Hill High School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Shelton | Foran | Shelton High School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Shepaug Valley | Northwestern | Shepaug Valley High School - Shepaug Valley Tennis Courts |
| MON 5/11 | 3:45 PM | League | South Windsor | Glastonbury | South Windsor High School - Wapping Tennis Courts |
| MON 5/11 | 3:45 PM | League | Southington | Berlin | Southington High School - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Stonington | NFA | Stonington High School - SHS Tennis Courts |
| MON 5/11 | 3:45 PM | League | Northwest Catholic | Simsbury | University of Saint Joseph - West Hartford - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Notre Dame Prep | Joel Barlow | Veteran's Park - Bridgeport - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Waterford | St. Bernard | Waterford High School - Tennis Courts - WHS |
| MON 5/11 | 3:45 PM | League | Mercy | Guilford | Wesleyan University - Tennis Courts |
| MON 5/11 | 3:45 PM | League | Weston | Brookfield | Weston High School - WHS Tennis Courts |
| MON 5/11 | 3:45 PM | League | East Catholic | E.O. Smith | Wickham Park - Wickham Park |
| MON 5/11 | 3:45 PM | League | Wilby | Woodland | Wilby High School - Dave Krill Tennis Courts at WHS |
| MON 5/11 | 3:45 PM | League | Windham | New London | Windham High School - WHS Courts |
| MON 5/11 | 4:00 PM | League | Coventry | Windsor Locks | Coventry High School - tennis courts |
| MON 5/11 | 4:00 PM | League | East Hampton | Portland | East Hampton High School - Tennis Courts |
| MON 5/11 | 4:00 PM | League | Lyman Memorial | Fitch | Lyman Memorial High School - Tennis Courts |
| MON 5/11 | 4:00 PM | League | Valley Regional | Old Saybrook | Valley Regional High School - Tennis Courts |
| MON 5/11 | 4:00 PM | Non-League | Cromwell | Westbrook | Cromwell Middle School - Waterous Park Tennis Courts |
| TUE 5/12 | 3:45 PM | League | Foran | Career Magnet | Foran High School - Foran Tennis Courts |
| TUE 5/12 | 3:45 PM | League | Hamden | Sheehan | Hamden Middle School - Tennis Courts |
| TUE 5/12 | 3:45 PM | League | West Haven | Branford | West Haven High School - West Haven Tennis Courts |
| TUE 5/12 | 3:45 PM | League | Westbrook | Coginchaug | Westbrook High School - Westbrook HS / MS Tennis Courts |
| WED 5/13 | 3:30 PM | League | Avon | Conard | Avon Middle School - Thompson Brook School |
| WED 5/13 | 3:30 PM | League | Kennedy | Crosby | John F. Kennedy High School - Chase Park |
| WED 5/13 | 3:30 PM | League | Seymour | Ansonia | Seymour High School - Tennis |
| WED 5/13 | 3:45 PM | League | Amity | Guilford | Amity Regional High School - Tennis Courts |
| WED 5/13 | 3:45 PM | League | Berlin | Rocky Hill | Berlin High School - Tennis Courts |
| WED 5/13 | 3:45 PM | League | Bolton | Granby Memorial | Bolton High School - BHS Tennis Courts |
| WED 5/13 | 3:45 PM | League | Bristol Central | Bloomfield | Bristol Central High School - Tennis Courts |
| WED 5/13 | 3:45 PM | League | Bristol Eastern | Lewis Mills | Bristol Eastern High School - Tennis Court |
| WED 5/13 | 3:45 PM | League | Brookfield | | Brookfield High School - BHS Tennis Courts |
| WED 5/13 | 3:45 PM | League | Cheshire | Jonathan Law | Cheshire High School - Tennis Courts |
| WED 5/13 | 3:45 PM | League | Coginchaug | Valley Regional | Coginchaug Regional High School - Tennis Courts @ CRHS |
| WED 5/13 | 3:45 PM | League | E.O. Smith | South Windsor | E.O. Smith High School - Tennis Courts |
| WED 5/13 | 3:45 PM | League | East Haven | Shelton | East Haven High School - Tennis Court |
| WED 5/13 | 3:45 PM | League | Farmington | Northwest Catholic | Farmington High School - Large Gymnasium |
| WED 5/13 | 3:45 PM | League | Glastonbury | Manchester | Glastonbury High School - Tennis Courts |
| WED 5/13 | 3:45 PM | League | Hall | Simsbury | Hall High School - Tennis Courts |
| WED 5/13 | 3:45 PM | League | Joel Barlow | New Fairfield | Joel Barlow High School - Tennis Courts |
| WED 5/13 | 3:45 PM | League | Killingly | Ledyard | Killingly High School - Tennis Courts |
| WED 5/13 | 3:45 PM | League | Maloney | New Britain | Maloney High School - Tennis Courts |
| WED 5/13 | 3:45 PM | League | Middletown | Plainville | Middletown Tennis Courts - Beman Tennis Courts |
| WED 5/13 | 3:45 PM | League | Montville | Lyman Memorial | Montville High School - Tennis Courts |
| WED 5/13 | 3:45 PM | League | Nonnewaug | Shepaug Valley | Nonnewaug High School - Tennis Courts |
| WED 5/13 | 3:45 PM | League | Platt | Newington | Platt High School - Tennis Court |
| WED 5/13 | 3:45 PM | League | Pomperaug | Notre Dame Prep | Pomperaug High School - PHS Tennis Courts |
| WED 5/13 | 3:45 PM | League | NFA | Woodstock Academy | Rec Fields - Armstrong Tennis Courts |
| WED 5/13 | 3:45 PM | League | Immaculate | New Milford | Rogers Park - Tennis Courts |
| WED 5/13 | 3:45 PM | League | Watertown | Wolcott | TBA - TBA |
| WED 5/13 | 3:45 PM | League | Tolland | East Hartford | Tolland High School - Tennis Courts |
| WED 5/13 | 3:45 PM | League | Gilbert | Northwestern | Walker Field - Tennis Courts |
| WED 5/13 | 3:45 PM | League | Weston | Stratford | Weston High School - WHS Tennis Courts |
| WED 5/13 | 3:45 PM | League | Wethersfield | Southington | Wethersfield High School - Tennis Courts |
| WED 5/13 | 3:45 PM | League | Wilby | Torrington | Wilby High School - Dave Krill Tennis Courts at WHS |
| WED 5/13 | 3:45 PM | League | Windsor | RHAM | Windsor High School - Tennis Courts |
| WED 5/13 | 3:45 PM | League | Windsor Locks | Canton | Windsor Locks High School - Tennis Court |
| WED 5/13 | 3:45 PM | League | Masuk | Bethel | Wolfe Park - Tennis Courts |
| WED 5/13 | 4:00 PM | League | Coventry | East Granby | Coventry High School - tennis courts |
| WED 5/13 | 4:00 PM | League | Ellington | Rockville | Ellington High School - Tennis Courts |
| WED 5/13 | 4:00 PM | League | Housatonic Regional | Lakeview | Housatonic Valley Regional High - Tennis Courts |
| WED 5/13 | 4:00 PM | League | New London | St. Bernard | New London High School - NLHS Tennis Courts |
| WED 5/13 | 4:00 PM | Non-League | Morgan | East Lyme | Morgan School - Tennis Courts |
| WED 5/13 | 5:00 AM | League | Enfield | East Catholic | Enfield High School - EHS TENNIS COURTS |
| THU 5/14 | 3:45 PM | League | Branford | Foran | Branford High School - Tennis Courts |
| THU 5/14 | 3:45 PM | League | Montville | Ledyard | Montville High School - Tennis Courts |
| THU 5/14 | 3:45 PM | League | Sheehan | East Haven | Sheehan High School - Sheehan HS Tennis Courts |
| THU 5/14 | 3:45 PM | Non-League | Fitch | Lyme-Old Lyme | Fitch High School - Main Tennis Courts |
| THU 5/14 | 3:45 PM | Non-League | Lewis Mills | Housatonic Regional | Lewis Mills High School - Tennis Courts |
| THU 5/14 | 3:45 PM | Non-League | Norwich Tech | Lyman Memorial | Norwich Technical High School - NTHS Outdoor Athletic Complex |
| THU 5/14 | 3:45 PM | Non-League | Immaculate | Abbott Tech | Rogers Park - Tennis Courts |
| THU 5/14 | 3:45 PM | Non-League | Shepaug Valley | New Fairfield | Shepaug Valley High School - Shepaug Valley Tennis Courts |
| THU 5/14 | 4:00 PM | League | Granby Memorial | Windsor Locks | Granby Memorial High School - Tennis Courts |
| THU 5/14 | 4:00 PM | Non-League | Coventry | Ellington | Coventry High School - tennis courts |
| FRI 5/15 | 12:01 AM | League | Woodstock Academy | St. Bernard | Pomfret School - Field House |
| FRI 5/15 | 3:45 PM | League | Cheshire | Mercy | Cheshire High School - Tennis Courts |
| FRI 5/15 | 3:45 PM | League | Lyman Hall | West Haven | Doolittle Park - Doolittle Tennis Courts |
| FRI 5/15 | 3:45 PM | League | Fitch | Killingly | Fitch High School - Main Tennis Courts |
| FRI 5/15 | 3:45 PM | League | North Branford | Westbrook | North Branford - NBHS Tennis Courts |
| FRI 5/15 | 3:45 PM | League | NFA | Windham | Rec Fields - Armstrong Tennis Courts |
| FRI 5/15 | 4:00 PM | League | New London | East Lyme | New London High School - NLHS Tennis Courts |
| SAT 5/16 | 11:00 AM | League | West Haven | Wilcox Tech | West Haven High School - West Haven Tennis Courts |
| MON 5/18 | 3:30 PM | League | Avon | Bristol Central | Avon Middle School - Thompson Brook School |
| MON 5/18 | 3:45 PM | League | Conard | Bloomfield | Conard High School - Tennis Courts |
| MON 5/18 | 3:45 PM | League | Coventry | Bolton | Coventry High School - tennis courts |
| MON 5/18 | 3:45 PM | League | Lyman Hall | East Haven | Doolittle Park - Doolittle Tennis Courts |
| MON 5/18 | 3:45 PM | League | East Granby | Windsor Locks | East Granby High School - EGHS Tennis Courts |
| MON 5/18 | 3:45 PM | League | East Hartford | East Catholic | East Hartford High School - Tennis Courts |
| MON 5/18 | 3:45 PM | League | Fitch | Stonington | Fitch High School - Main Tennis Courts |
| MON 5/18 | 3:45 PM | League | Glastonbury | Windsor | Glastonbury High School - Tennis Courts |
| MON 5/18 | 3:45 PM | League | Lewis Mills | Farmington | Lewis Mills High School - Tennis Courts |
| MON 5/18 | 3:45 PM | League | Maloney | Berlin | Maloney High School - Tennis Courts |
| MON 5/18 | 3:45 PM | League | New Britain | Rocky Hill | New Britain High School - tennis courts |
| MON 5/18 | 3:45 PM | League | Newington | Southington | Newington High School - Tennis Courts |
| MON 5/18 | 3:45 PM | League | North Branford | Valley Regional | North Branford - NBHS Tennis Courts |
| MON 5/18 | 3:45 PM | League | Plainville | Platt | Plainville High School - PHS Tennis Courts |
| MON 5/18 | 3:45 PM | League | Simsbury | Bristol Eastern | Simsbury High School - Tennis Courts |
| MON 5/18 | 3:45 PM | League | South Windsor | Manchester | South Windsor High School - Wapping Tennis Courts |
| MON 5/18 | 3:45 PM | League | Tolland | Enfield | Tolland High School - Tennis Courts |
| MON 5/18 | 3:45 PM | League | Northwest Catholic | Hall | University of Saint Joseph - West Hartford - Tennis Courts |
| MON 5/18 | 3:45 PM | League | Wethersfield | Middletown | Wethersfield High School - Tennis Courts |
| MON 5/18 | 4:00 PM | League | Lyman Memorial | Waterford | Lyman Memorial High School - Tennis Courts |
| MON 5/18 | 4:00 PM | Non-League | Guilford | East Lyme | Guilford High School - GHS Tennis Courts |
| MON 5/18 | 4:00 PM | Non-League | Westbrook | Cromwell | Westbrook High School - Westbrook HS / MS Tennis Courts |
| TUE 5/19 | 3:45 PM | League | Foran | Jonathan Law | Foran High School - Foran Tennis Courts |
| TUE 5/19 | 3:45 PM | League | RHAM | E.O. Smith | RHAM High School - Tennis Courts |
| TUE 5/19 | 4:00 PM | Non-League | Rockville | Tolland | Rockville High School - RHS Tennis Courts |
| WED 5/20 | 12:00 PM | Postseason | Joel Barlow | New Milford, Bunnell, New Fairfield, Masuk, Immaculate, Brookfield, Weston, Notre Dame Prep, Stratford, Bassick, Harding, Bethel, Newtown, Pomperaug | Joel Barlow High School - Tennis Courts |
| WED 5/20 | 3:45 PM | League | Berlin | New Britain | Berlin High School - Tennis Courts |
| WED 5/20 | 3:45 PM | League | Bristol Central | Conard | Bristol Central High School - Tennis Courts |
| WED 5/20 | 3:45 PM | League | Bristol Eastern | Avon | Bristol Eastern High School - Tennis Court |
| WED 5/20 | 3:45 PM | League | Bloomfield | Northwest Catholic | Carmen Arace Middle School - Tennis Courts |
| WED 5/20 | 3:45 PM | League | E.O. Smith | Glastonbury | E.O. Smith High School - Tennis Courts |
| WED 5/20 | 3:45 PM | League | Enfield | East Hartford | Enfield High School - EHS TENNIS COURTS |
| WED 5/20 | 3:45 PM | League | Farmington | Simsbury | Farmington High School - Large Gymnasium |
| WED 5/20 | 3:45 PM | League | Hall | Lewis Mills | Hall High School - Tennis Courts |
| WED 5/20 | 3:45 PM | League | Jonathan Law | Lyman Hall | Jonathan Law High School - Tennis Courts |
| WED 5/20 | 3:45 PM | League | Manchester | RHAM | Manchester High School - Manchester |
| WED 5/20 | 3:45 PM | League | Middletown | Maloney | Middletown Tennis Courts - Beman Tennis Courts |
| WED 5/20 | 3:45 PM | League | Platt | Wethersfield | Platt High School - Tennis Court |
| WED 5/20 | 3:45 PM | League | Rocky Hill | Newington | Rocky Hill High School |
| WED 5/20 | 3:45 PM | League | East Catholic | South Windsor | Wickham Park - Wickham Park |
| WED 5/20 | 3:45 PM | League | Windsor | Tolland | Windsor High School - Tennis Courts |
| THU 5/21 | 12:00 PM | Postseason | Joel Barlow | Immaculate, Masuk, Brookfield, New Fairfield, Bunnell, New Milford, Weston, Notre Dame Prep, Stratford, Bethel, Harding, Bassick, Pomperaug, Newtown | Joel Barlow High School - Tennis Courts |
| THU 5/21 | 3:15 PM | League | Conard | Hall | Conard High School - Tennis Courts |
| THU 5/21 | 3:45 PM | League | Lyme-Old Lyme | Waterford | Lyme-Old Lyme High School - Tennis Courts |
| THU 5/21 | 3:45 PM | League | Southington | Plainville | Southington High School - Tennis Courts |
| THU 5/21 | 3:45 PM | League | Tolland | E.O. Smith | Tolland High School - Tennis Courts |
| THU 5/21 | 8:00 AM | Postseason | Housatonic Regional | Shepaug Valley, Northwestern, Thomaston, Lakeview, Gilbert, Nonnewaug | TBA - TBA |
| FRI 5/22 | 3:30 PM | League | Avon | Farmington | Avon Middle School - Thompson Brook School |
| FRI 5/22 | 3:45 PM | League | Bristol Eastern | Bristol Central | Bristol Eastern High School - Tennis Court |
| FRI 5/22 | 3:45 PM | League | East Hartford | Manchester | East Hartford High School - Tennis Courts |
| FRI 5/22 | 3:45 PM | League | Lewis Mills | Northwest Catholic | Lewis Mills High School - Tennis Courts |
| FRI 5/22 | 3:45 PM | League | Maloney | Platt | Maloney High School - Tennis Courts |
| FRI 5/22 | 3:45 PM | League | Middletown | Berlin | Middletown Tennis Courts - Beman Tennis Courts |
| FRI 5/22 | 3:45 PM | League | New Britain | Southington | New Britain High School - tennis courts |
| FRI 5/22 | 3:45 PM | League | Plainville | Newington | Plainville High School - PHS Tennis Courts |
| FRI 5/22 | 3:45 PM | League | RHAM | South Windsor | RHAM High School - Tennis Courts |
| FRI 5/22 | 3:45 PM | League | Rocky Hill | Wethersfield | Rocky Hill High School |
| FRI 5/22 | 3:45 PM | League | Simsbury | Bloomfield | Simsbury High School - Tennis Courts |
| FRI 5/22 | 3:45 PM | League | East Catholic | Glastonbury | Wickham Park - Wickham Park |
| FRI 5/22 | 3:45 PM | League | Windsor | Enfield | Windsor High School - Tennis Courts |
| SAT 5/23 | 10:00 AM | Non-League | North Branford | Wilcox Tech | North Branford - NBHS Tennis Courts |
| TUE 5/26 | 12:01 AM | Postseason | Housatonic Regional | Thomaston, Lakeview, Northwestern, Shepaug Valley, Nonnewaug, Gilbert | TBA - TBA |
| TUE 5/26 | 4:00 PM | Non-League | Lakeview | Pomperaug | Lakeview Regional High School - Tennis Courts |