| Date | Time | Type | Home School | Away School | Site |
| THU 8/24 | 4:00 PM | Scrimmage | Newtown | Bethel | Newtown High School - Blue and Gold Stadium |
| THU 8/24 | 5:30 PM | League | Staples | Fairfield Prep, Fairfield Ludlowe, Wilton | Staples High School - Staples Stadium |
| SAT 8/26 | 10:30 AM | Scrimmage | Fairfield Prep | Ridgefield | Fairfield University - Rafferty Stadium |
| SAT 8/26 | 9:00 AM | Scrimmage | Simsbury | Norwalk | Holden Field - Turf |
| MON 8/28 | 4:30 PM | Scrimmage | Westhill | Norwalk | Westhill High School - J. Walter Kennedy Stadium |
| MON 8/28 | 4:30 PM | Scrimmage | Windsor | Stratford | Windsor High School - Sage Park Middle School Grass Field |
| WED 8/30 | 6:00 PM | Scrimmage | Staples | Shelton | Staples High School - Staples Stadium |
| THU 8/31 | 3:30 PM | Scrimmage | Manchester | Glastonbury, South Windsor | Memorial Field @ MHS - Memorial Field @ MHS |
| THU 8/31 | 4:00 PM | Scrimmage | Newtown | Fairfield Warde | Newtown High School - Back Turf Field |
| THU 8/31 | 4:00 PM | Scrimmage | St. Joseph | Fairfield Ludlowe | St. Joseph High School - Upper Turf |
| THU 8/31 | 4:00 PM | Scrimmage | Trumbull | Darien | Trumbull High School - Field 14 |
| THU 8/31 | 5:30 PM | Scrimmage | Pomperaug | Oxford | Pomperaug High School - Football Practice Field |
| FRI 9/1 | 4:00 PM | Scrimmage | New Canaan | Greenwich | New Canaan HS - WTT #1 |
| FRI 9/1 | 5:00 PM | League | Stamford | Brien McMahon | Stamford High School - Boyle Stadium |
| FRI 9/1 | 9:00 AM | Scrimmage | Newington | New Britain | Newington High School - Abbate Field, Alumni Rd. |
| SAT 9/2 | 10:00 AM | Scrimmage | North Haven | Daniel Hand | North Haven Middle School - East Turf Field |
| WED 9/6 | 6:00 PM | Scrimmage | Manchester | Enfield | Memorial Field @ MHS - Memorial Field @ MHS |
| WED 9/6 | Canceled | League | South Windsor | E.O. Smith | South Windsor High School - Field in front of HS |
| WED 9/6 | Postponed | Scrimmage | Amity | Ansonia | Amity Regional High School - William Johnson Stadium Field |
| WED 9/6 | Postponed | Scrimmage | Pomperaug | Sheehan | Pomperaug High School - Stadium |
| THU 9/7 | 6:00 PM | League | Brien McMahon | Platt Tech | Brien McMahon High School - Casagrande Field |
| THU 9/7 | 6:30 PM | Non-League | Xavier | Fairfield Warde | Xavier High School - Larry McHugh Field |
| THU 9/7 | 7:00 PM | Non-League | North Haven | Darien | North Haven Middle School - Vanacore Field |
| THU 9/7 | Canceled | League | Bristol Eastern | Farmington | Bristol Eastern High School - Alumni Field-Turf |
| THU 9/7 | Canceled | League | Norwalk | Wilbur Cross | Nathan Hale MS - Callahan Complex at Nathan Hale Lower |
| THU 9/7 | Canceled | League | Windsor | Bristol Central | Windsor High School - Sage Park Middle School Grass Field |
| THU 9/7 | Canceled | Non-League | Platt | Newington | Platt High School - Platt Turf field |
| THU 9/7 | Postponed | League | Cheshire | Ridgefield | Cheshire High Main Game field - Cheshire High Main Game field |
| THU 9/7 | Postponed | League | East Hartford | Maloney | East Hartford High School - Freshman Practice Field |
| THU 9/7 | Postponed | League | Staples | West Haven | Staples High School - Staples Stadium |
| THU 9/7 | Postponed | Non-League | Seymour | Shelton | Seymour High School - turf field |
| THU 9/7 | Postponed | Non-League | Notre Dame-West Haven | New Milford | Veterans Memorial Park (West Haven, CT) - Field |
| FRI 9/8 | 6:00 PM | League | Fairfield Prep | Greenwich | Fairfield University - Rafferty Stadium |
| FRI 9/8 | Canceled | League | Hillhouse | Foran | Bowen Field - Football Field |
| SAT 9/9 | 10:00 AM | League | Hamden | Trumbull | Hamden High School - HHS Turf #1 |
| SAT 9/9 | 10:00 AM | League | Berlin | Avon | Sage Park Berlin - Scalise Field |
| SAT 9/9 | 10:00 AM | Non-League | Masuk | Wilton | Masuk High School - Benedict Stadium Field @ Masuk HS |
| SAT 9/9 | 10:00 AM | Non-League | Newtown | St. Joseph | Newtown High School - NHS Back Turf Field |
| SAT 9/9 | 10:30 AM | League | Northwest United | East Lyme | Nonnewaug High School - Turf Field |
| SAT 9/9 | 11:00 AM | League | Stamford | Brien McMahon | Stamford High School - Boyle Stadium |
| SAT 9/9 | 11:00 AM | League | Wilby | Oxford | Wilby High School - Football Field |
| SAT 9/9 | 11:00 AM | Non-League | Danbury | Glastonbury | Danbury High School - Stadium Turf Field |
| SAT 9/9 | 12:00 PM | League | New Canaan | Stamford | New Canaan HS - Dunning Stadium |
| SAT 9/9 | 12:00 PM | Non-League | Fairfield Ludlowe | Simsbury | Fairfield Ludlowe High School - Taft Field |
| SAT 9/9 | 5:00 PM | League | Maloney | Platt | Maloney High School - Turf Field |
| SAT 9/9 | 8:00 AM | League | Conard | Middletown | Conard High School - Football Field - Grass |
| SAT 9/9 | 8:00 AM | League | Enfield | Manchester | Enfield High School - EHS TURF |
| SAT 9/9 | 8:00 AM | League | Wethersfield | Hall | Wethersfield High School - Cottone Field |
| SAT 9/9 | Canceled | League | Kennedy | WCA | Kennedy High School (Waterbury) - Kennedy High School (Waterbury) |
| SAT 9/9 | Postponed | League | Crosby | Torrington | Crosby High School - CHS - Jimmy Lee Stadium (Turf) |
| SAT 9/9 | Postponed | League | Naugatuck | Wolcott | Naugatuck High School - Veterans Field |
| MON 9/11 | 6:30 PM | League | Northwest United | Wilcox Tech | Nonnewaug High School - Turf Field |
| TUE 9/12 | 6:30 PM | League | Northwest United | Wilcox Tech | Nonnewaug High School - Turf Field |
| WED 9/13 | 4:30 PM | League | St. Joseph | Westhill | St. Joseph High School - Upper Turf |
| WED 9/13 | 7:00 PM | League | Notre Dame-West Haven | Ansonia | Notre Dame High School - Side Turf |
| WED 9/13 | Canceled | League | Jonathan Law | West Haven | Jonathan Law High School - Lawmen Stadium |
| WED 9/13 | Canceled | League | Lyman Hall | Wilbur Cross | Lyman Hall High School - Fitzgerald Field |
| WED 9/13 | Postponed | League | Amity | West Haven | Amity Regional High School - William Johnson Stadium Field |
| WED 9/13 | Postponed | League | Windsor | Hall | Windsor High School - Jack O'Brien Stadium |
| THU 9/14 | 2:45 PM | League | South Windsor | Platt | South Windsor High School - Field in front of HS |
| THU 9/14 | 3:30 PM | League | Middletown | Glastonbury | Middletown High School - MHS Stadium |
| THU 9/14 | 3:30 PM | League | Trumbull | Staples | Trumbull High School - Cork Field |
| THU 9/14 | 3:45 PM | League | Conard | Manchester | Conard High School - Football Field - Grass |
| THU 9/14 | 3:45 PM | League | Enfield | East Hartford | Enfield High School - EHS TURF |
| THU 9/14 | 3:45 PM | League | Wethersfield | Southington | Samuel B. Webb Elementary School - Webb Field |
| THU 9/14 | 3:45 PM | League | New Britain | Bristol Central | Veteran's Stadium-Willow Brook Park - Football Field |
| THU 9/14 | 4:00 PM | League | Darien | Wilton | Darien High School - DHS Stadium East |
| THU 9/14 | 4:00 PM | League | Norwalk | Danbury | Nathan Hale MS - Callahan Complex at Nathan Hale Lower |
| THU 9/14 | 4:00 PM | League | New Milford | Newtown | New Milford High School - North Turf Field - NMHS |
| THU 9/14 | 4:00 PM | League | Ridgefield | Greenwich | Ridgefield High School - Tiger Hollow Turf Field II |
| THU 9/14 | 4:00 PM | League | Shelton | Cheshire | Shelton High School - Finn Stadium |
| THU 9/14 | 4:00 PM | Non-League | Seymour | Pomperaug | Seymour High School - turf field |
| THU 9/14 | 5:00 PM | League | Brien McMahon | Fairfield Warde | Brien McMahon High School - Casagrande Field |
| THU 9/14 | 6:00 PM | League | Daniel Hand | Fairfield Prep | Daniel Hand High School - Turf Field |
| THU 9/14 | 7:00 PM | League | Fairfield Ludlowe | New Canaan | Fairfield Ludlowe High School - Taft Field |
| THU 9/14 | 7:00 PM | League | Masuk | Stratford | Masuk High School - Benedict Stadium Field @ Masuk HS |
| THU 9/14 | Canceled | League | Harding | Xavier | Warren Harding High School - Lewis Field |
| FRI 9/15 | 3:45 PM | League | Newington | Maloney | Newington High School - Abbate Field, Alumni Rd. |
| SAT 9/16 | 1:00 PM | League | Naugatuck | Holy Cross | Naugatuck High School - Veterans Field |
| SAT 9/16 | 10:00 AM | League | Simsbury | Berlin | Holden Field - Turf |
| SAT 9/16 | 11:00 AM | League | WCA | Oxford | Waterbury Career Academy - Football Field |
| SAT 9/16 | 11:00 AM | League | Wilby | Watertown | Wilby High School - Football Field |
| SAT 9/16 | Canceled | League | Torrington | St. Paul Catholic | Torrington High School - Robert Frost Sports Complex |
| WED 9/20 | 3:30 PM | League | Seymour | Ansonia | Seymour High School - turf field |
| WED 9/20 | 5:30 PM | League | Brien McMahon | Westhill | Brien McMahon High School - Casagrande Field |
| THU 9/21 | 3:45 PM | League | Bristol Eastern | Berlin | Bristol Eastern High School - Practice Football Field |
| THU 9/21 | 3:45 PM | League | Farmington | Stratford | Farmington High School - Turf Field |
| THU 9/21 | 3:45 PM | League | Hall | E.O. Smith | Hall High School - Football Practice Field |
| THU 9/21 | 3:45 PM | League | Platt | Manchester | Platt High School - Platt Turf field |
| THU 9/21 | 3:45 PM | Non-League | Enfield | Rockville | Enfield High School - EHS TURF |
| THU 9/21 | 3:45 PM | Non-League | Newington | Conard | Newington High School - Abbate Field, Alumni Rd. |
| THU 9/21 | 4:00 PM | League | North Haven | Sheehan | North Haven Middle School - Vanacore Field |
| THU 9/21 | 4:00 PM | League | Xavier | Daniel Hand | Xavier High School - Larry McHugh Field |
| THU 9/21 | 4:00 PM | Non-League | Glastonbury | Cheshire | Glastonbury High School - Turf Field |
| THU 9/21 | 4:00 PM | Non-League | South Windsor | Prince Tech-Innovation | South Windsor High School - Field in front of HS |
| THU 9/21 | 4:00 PM | Non-League | Newtown | Trumbull | Treadwell Park - Newtown Treadwell Park |
| THU 9/21 | 4:00 PM | Non-League | Notre Dame-West Haven | St. Joseph | Veterans Memorial Park (West Haven, CT) - Field |
| THU 9/21 | 4:15 PM | League | Wilton | Joel Barlow | Wilton High School - Fuijitani Field -Turf |
| THU 9/21 | 4:15 PM | Non-League | Darien | Fairfield Prep | Darien High School - Royle Field @ 133 Mansfield Ave, Darien, CT 06820 |
| THU 9/21 | 4:30 PM | Non-League | Avon | East Lyme | Avon High School - Turf Field |
| THU 9/21 | 4:30 PM | Non-League | Fairfield Warde | Bristol Central | Fairfield Warde High School - Tetreau/Davis Field |
| THU 9/21 | 5:00 PM | League | East Hartford | Danbury | East Hartford High School - Turf Field |
| THU 9/21 | 5:00 PM | League | Maloney | Greenwich | Falcon Field (Meriden, CT) - Football Field |
| THU 9/21 | 5:00 PM | League | Stamford | Simsbury | Stamford High School - Boyle Stadium |
| THU 9/21 | 5:30 PM | League | Hamden | Fairfield Ludlowe | Hamden High School - HHS Turf #1 |
| THU 9/21 | 5:30 PM | Non-League | New Milford | Middletown | New Milford High School - North Turf Field - NMHS |
| THU 9/21 | 5:30 PM | Non-League | Norwalk | Pomperaug | Norwalk High School - Testa Field |
| THU 9/21 | 6:00 PM | League | Cheney Tech | Wilcox Tech | Cheney Tech. - Football Field |
| THU 9/21 | 6:00 PM | League | Southington | Staples | Southington High School - 3 TURF FIELD |
| THU 9/21 | 6:30 PM | League | Ridgefield | West Haven | Ridgefield High School - Tiger Hollow Turf Field II |
| THU 9/21 | Canceled | League | Amity | Jonathan Law | Amity Regional High School - William Johnson Stadium Field |
| THU 9/21 | Canceled | League | Wilbur Cross | Sheehan | Wilbur Cross High School - Wilbur Cross Athletic Complex |
| SAT 9/23 | 11:00 AM | League | Wolcott | Naugatuck | Wolcott High School - Turf Field |
| SAT 9/23 | 9:00 AM | League | Wethersfield | Shelton | Wethersfield High School - Cottone Field |
| SAT 9/23 | Canceled | League | Northwest United | Platt Tech | Nonnewaug High School - Turf Field |
| MON 9/25 | 6:00 PM | League | Northwest United | Wilcox Tech | Nonnewaug High School - football field |
| WED 9/27 | 3:45 PM | League | Avon | Platt | Avon High School - Turf Field |
| WED 9/27 | 3:45 PM | League | Pomperaug | New Milford | Pomperaug High School - Stadium |
| WED 9/27 | 4:00 PM | League | Xavier | Sheehan | Xavier High School - Larry McHugh Field |
| WED 9/27 | 5:30 PM | League | Joel Barlow | Brookfield | Joel Barlow High School - Field I (Stadium) |
| WED 9/27 | Postponed | League | Lyman Hall | Amity | Lyman Hall High School - Fitzgerald Field |
| THU 9/28 | 3:30 PM | League | Middletown | Windsor | Middletown High School - MHS Stadium |
| THU 9/28 | 3:45 PM | League | Bristol Central | Rockville | Bristol Central High School - BC Turf Field |
| THU 9/28 | 3:45 PM | League | Bristol Eastern | South Windsor | Bristol Eastern High School - Practice Football Field |
| THU 9/28 | 3:45 PM | League | Enfield | Farmington | Enfield High School - EHS TURF |
| THU 9/28 | 3:45 PM | League | Hall | Southington | Hall High School - Football Practice Field |
| THU 9/28 | 3:45 PM | League | Maloney | Simsbury | Maloney High School - Turf Field |
| THU 9/28 | 3:45 PM | League | Manchester | Newington | Memorial Field @ MHS - Memorial Field @ MHS |
| THU 9/28 | 3:45 PM | League | Platt Tech | ATI | ORANGE AVE ATHLETIC COMPLEX - ORANGE AVE ATHLETIC COMPLEX - Field 1 (Soccer) |
| THU 9/28 | 4:00 PM | League | Danbury | Fairfield Warde | Danbury High School - Stadium Turf Field |
| THU 9/28 | 4:00 PM | League | Darien | Trumbull | Royle School Field - Royle School Field |
| THU 9/28 | 4:00 PM | League | St. Joseph | Ridgefield | St. Joseph High School - Upper Turf |
| THU 9/28 | 4:00 PM | League | Notre Dame-West Haven | North Haven | Veterans Memorial Park (West Haven, CT) - Field |
| THU 9/28 | 4:30 PM | League | Newtown | Stratford | Newtown High School - NHS Back Turf Field |
| THU 9/28 | 4:30 PM | League | Shelton | West Haven | Shelton High School - Finn Stadium |
| THU 9/28 | 4:30 PM | League | Wilton | Greenwich | Wilton High School - Fuijitani Field -Turf |
| THU 9/28 | 5:00 PM | League | Brien McMahon | Stamford | Brien McMahon High School - Casagrande Field |
| THU 9/28 | 5:00 PM | League | New Britain | Conard | Veteran's Stadium-Willow Brook Park - Football Field |
| THU 9/28 | 5:15 PM | Non-League | Seymour | Masuk | Seymour High School - turf field |
| THU 9/28 | 5:30 PM | League | Hamden | Ansonia | Hamden High School - HHS Turf #1 |
| THU 9/28 | 6:00 PM | League | Cheshire | Fairfield Prep | Cheshire High Main Game field - Cheshire High Main Game field |
| THU 9/28 | 6:00 PM | League | Daniel Hand | Guilford | Daniel Hand High School - Turf Field |
| THU 9/28 | 6:00 PM | League | Staples | New Canaan | Staples High School - Staples Stadium |
| THU 9/28 | 7:00 PM | League | Fairfield Ludlowe | Norwalk | Fairfield Ludlowe High School - Taft Field |
| FRI 9/29 | 3:45 PM | League | Glastonbury | East Hartford | Glastonbury High School - Turf Field |
| SAT 9/30 | 10:00 AM | League | Naugatuck | Watertown | Naugatuck High School - Veterans Field |
| SAT 9/30 | 11:00 AM | League | Wolcott | Wilby | Wolcott High School - Turf Field |
| SAT 9/30 | 2:30 PM | League | Berlin | Wethersfield | Sage Park Berlin - Scalise Field |
| MON 10/2 | 4:45 PM | Non-League | | Stafford, East Windsor, Somers | Minnechaug Reg High School - MRHS Track and Field |
| WED 10/4 | 3:45 PM | League | Enfield | Newington | Enfield High School - EHS TURF |
| WED 10/4 | 3:45 PM | League | Manchester | Middletown | Memorial Field @ MHS - Memorial Field @ MHS |
| WED 10/4 | 5:00 PM | Non-League | Stratford | Ansonia | Penders Field - Penders Field - Stratford |
| THU 10/5 | 3:45 PM | League | Conard | Southington | Conard High School - Football Field - Grass |
| THU 10/5 | 3:45 PM | League | Simsbury | East Hartford | Holden Field - Turf |
| THU 10/5 | 3:45 PM | League | E.O. Smith | Avon | Mansfield Middle School - Spring Hill Ball Field |
| THU 10/5 | 3:45 PM | Non-League | Platt | Wilcox Tech | Platt High School - Platt Turf field |
| THU 10/5 | 4:00 PM | League | Amity | Cheshire | Amity Regional High School - William Johnson Stadium Field |
| THU 10/5 | 4:00 PM | League | Darien | Fairfield Ludlowe | Darien High School - Royle Field @ 133 Mansfield Ave, Darien, CT 06820 |
| THU 10/5 | 4:00 PM | League | Fairfield Prep | North Haven | Fairfield University - Rafferty Stadium |
| THU 10/5 | 4:00 PM | League | Shelton | Notre Dame-West Haven | Shelton High School - Finn Stadium |
| THU 10/5 | 4:00 PM | League | St. Joseph | Masuk | St. Joseph High School - Upper Turf |
| THU 10/5 | 4:30 PM | League | Fairfield Warde | Brien McMahon | Fairfield Warde High School - Tetreau/Davis Field |
| THU 10/5 | 5:00 PM | League | Foran | Sheehan | Foran High School - Foran High School - Turf Field |
| THU 10/5 | 5:00 PM | League | New Britain | Hall | Veteran's Stadium-Willow Brook Park - Football Field |
| THU 10/5 | 5:30 PM | League | Hamden | West Haven | Hamden High School - HHS Turf #1 |
| THU 10/5 | Canceled | League | Hartford Public | Windsor | Hartford Public High School - Football Field |
| THU 10/5 | Canceled | League | Lyman Hall | Harding | Lyman Hall High School - Fitzgerald Field |
| THU 10/5 | Canceled | League | Platt Tech | Thames River Crusaders | Orange Ave. Athletic Complex - Football Field |
| THU 10/5 | Canceled | League | Wethersfield | Bristol Eastern | Samuel B. Webb Elementary School - Webb Field |
| THU 10/5 | Canceled | League | Wilbur Cross | Daniel Hand | Wilbur Cross High School - Wilbur Cross Athletic Complex |
| FRI 10/6 | 3:45 PM | League | Bristol Central | Berlin | Bristol Central High School - BC Turf Field |
| FRI 10/6 | 3:45 PM | League | Glastonbury | Maloney | Glastonbury High School - Turf Field |
| SAT 10/7 | 11:00 AM | Non-League | Wilby | Northwest United | Wilby High School - Football Field |
| SAT 10/7 | 8:00 AM | League | Wethersfield | SMSA Co-op | Wethersfield High School - Cottone Field |
| MON 10/9 | 3:45 PM | League | Crosby | Watertown | Crosby High School - CHS - Jimmy Lee Stadium (Turf) |
| TUE 10/10 | 6:00 PM | League | Naugatuck | GNH | Naugatuck High School - Veterans Field |
| WED 10/11 | 5:00 PM | League | Stratford | New Milford | Penders Field - Penders Field - Stratford |
| WED 10/11 | Postponed | League | Joel Barlow | Masuk | Joel Barlow High School - Field I (Stadium) |
| THU 10/12 | 3:45 PM | League | Amity | West Haven | Amity Regional High School - William Johnson Stadium Field |
| THU 10/12 | 3:45 PM | League | Farmington | South Windsor | Farmington High School - Turf Field |
| THU 10/12 | 4:00 PM | League | Greenwich | St. Joseph | Greenwich High School - Field 7 |
| THU 10/12 | 4:30 PM | League | Fairfield Warde | Norwalk | Fairfield Warde High School - Tetreau/Davis Field |
| THU 10/12 | 4:30 PM | League | Shelton | Fairfield Prep | Shelton High School - Finn Stadium |
| THU 10/12 | 5:00 PM | League | Danbury | Westhill | Danbury High School - Stadium Turf Field |
| THU 10/12 | 5:00 PM | League | Stamford | Fairfield Ludlowe | Stamford High School - Boyle Stadium |
| THU 10/12 | 5:00 PM | Non-League | Newtown | Daniel Hand | Newtown High School - NHS Back Turf Field |
| THU 10/12 | 5:30 PM | League | Hamden | Cheshire | Hamden High School - HHS Turf #1 |
| THU 10/12 | 6:00 PM | League | Staples | Wilton | Staples High School - Staples Stadium |
| THU 10/12 | 6:30 PM | League | Ridgefield | Darien | Ridgefield High School - Tiger Hollow Turf Field II |
| THU 10/12 | 6:30 PM | League | Southington | New Britain | Southington High School - 3 TURF FIELD |
| THU 10/12 | 7:00 PM | League | New Canaan | Trumbull | New Canaan HS - Dunning Stadium |
| THU 10/12 | Canceled | League | Lyman Hall | Hillhouse | Lyman Hall High School - Fitzgerald Field |
| THU 10/12 | Canceled | League | Harding | Guilford | Warren Harding High School - Lewis Field |
| THU 10/12 | Postponed | League | Killingly | Rockville | Killingly High School - Morgan Field |
| SAT 10/14 | 10:00 AM | League | Pomperaug | ATI | Pomperaug High School - Stadium |
| MON 10/16 | 6:00 PM | League | Northwest United | Wilcox Tech | Nonnewaug High School - Turf Field |
| WED 10/18 | 4:30 PM | League | Platt | Plainville | Platt High School - Platt Turf field |
| WED 10/18 | 4:45 PM | League | Wilby | Crosby | Wilby High School - Football Field |
| WED 10/18 | 5:00 PM | League | Danbury | Stamford | Danbury High School - Stadium Turf Field |
| WED 10/18 | 5:30 PM | League | Brien McMahon | Trumbull | Brien McMahon High School - Casagrande Field |
| WED 10/18 | Canceled | League | | Hartford Public | Memorial Field @ MHS - Memorial Field @ MHS |
| THU 10/19 | 3:00 PM | Non-League | Enfield | Berlin | Enfield High School - EHS TURF |
| THU 10/19 | 3:15 PM | League | Glastonbury | Hall | Glastonbury High School - Turf Field |
| THU 10/19 | 3:30 PM | Non-League | Platt Tech | Foran | ORANGE AVE ATHLETIC COMPLEX - ORANGE AVE ATHLETIC COMPLEX - Field 2 (Football) |
| THU 10/19 | 3:45 PM | League | Conard | Simsbury | Conard High School - Football Field - Grass |
| THU 10/19 | 3:45 PM | League | Maloney | New Britain | Maloney High School - Turf Field |
| THU 10/19 | 3:45 PM | League | South Windsor | Bristol Central | South Windsor High School - Field in front of HS |
| THU 10/19 | 3:45 PM | League | Windsor | Newington | Windsor High School - Jack O'Brien Stadium |
| THU 10/19 | 4:00 PM | League | Westhill | Darien | Rippowan MS - Rippowam Turf Field |
| THU 10/19 | 4:00 PM | League | St. Joseph | Norwalk | St. Joseph High School - Upper Turf |
| THU 10/19 | 4:00 PM | League | Notre Dame-West Haven | Daniel Hand | Veterans Memorial Park (West Haven, CT) - Field |
| THU 10/19 | 4:00 PM | League | Xavier | Amity | Xavier High School - Larry McHugh Field |
| THU 10/19 | 4:30 PM | League | Greenwich | New Canaan | Greenwich High School - Field 7 |
| THU 10/19 | 4:30 PM | League | Wilton | Fairfield Ludlowe | Wilton High School - Fuijitani Field -Turf |
| THU 10/19 | 4:30 PM | Non-League | Newtown | Sheehan | Newtown High School - NHS Back Turf Field |
| THU 10/19 | 6:00 PM | League | Staples | Ridgefield | Staples High School - Staples Stadium |
| THU 10/19 | 6:30 PM | League | Southington | East Hartford | Southington High School - 3 TURF FIELD |
| THU 10/19 | Canceled | League | Bristol Eastern | Platt | Bristol Eastern High School - Practice Football Field |
| THU 10/19 | Canceled | League | Northwest Catholic | Berlin | Northwest Catholic High School (Primary) - NWC Lacrosse Field |
| THU 10/19 | Canceled | League | Harding | Hillhouse | Warren Harding High School - Lewis Field |
| THU 10/19 | Canceled | League | Wilbur Cross | Notre Dame-West Haven | Wilbur Cross High School - Wilbur Cross Athletic Complex |
| THU 10/19 | Postponed | League | Pomperaug | Masuk | Pomperaug High School - Stadium |
| FRI 10/20 | Canceled | League | E.O. Smith | Enfield | Mansfield Middle School - Spring Hill Ball Field |
| FRI 10/20 | Canceled | League | North Haven | West Haven | North Haven Middle School - Vanacore Field |
| SAT 10/21 | 10:00 AM | League | Bloomfield | Manchester | Bloomfield High School - Phil Rubin Stadium- Turf Field & Track |
| SAT 10/21 | 11:00 AM | League | Wolcott | Seymour | Wolcott High School - Turf Field |
| SAT 10/21 | 11:30 AM | League | Avon | Farmington | Avon High School - Turf Field |
| SAT 10/21 | 8:00 AM | League | Wethersfield | Middletown | Wethersfield High School - Cottone Field |
| MON 10/23 | 6:00 PM | League | Northwest United | Oxford | Nonnewaug High School - Turf Field |
| MON 10/23 | 6:00 PM | League | Torrington | WCA | Torrington High School - Torrington High School |
| WED 10/25 | 3:45 PM | League | Platt | Berlin | Platt High School - Platt Turf field |
| WED 10/25 | 4:00 PM | League | Manchester | South Windsor | Memorial Field @ MHS - Memorial Field @ MHS |
| WED 10/25 | 7:00 PM | Non-League | Fairfield Ludlowe | Platt Tech | Fairfield Ludlowe High School - Taft Field |
| THU 10/26 | 3:00 PM | Non-League | Rockville | Killingly | Rockville High School - Stadium Field |
| THU 10/26 | 3:30 PM | League | Pomperaug | Stratford | Pomperaug High School - Stadium |
| THU 10/26 | 3:45 PM | League | Newington | Middletown | Alumni Field - Baseball Diamond |
| THU 10/26 | 3:45 PM | League | Bristol Central | Wethersfield | Bristol Central High School - BC Turf Field |
| THU 10/26 | 3:45 PM | League | East Hartford | Conard | East Hartford High School - Freshman Practice Field |
| THU 10/26 | 3:45 PM | League | Enfield | Windsor | Enfield High School - EHS TURF |
| THU 10/26 | 3:45 PM | League | Fairfield Prep | Hamden | Fairfield University - Rafferty Stadium |
| THU 10/26 | 3:45 PM | League | Hall | Maloney | Hall High School - Football Practice Field |
| THU 10/26 | 3:45 PM | League | Simsbury | Southington | Holden Field - Turf |
| THU 10/26 | 3:45 PM | League | E.O. Smith | Farmington | Mansfield Middle School - Spring Hill Ball Field |
| THU 10/26 | 3:45 PM | League | New Britain | Glastonbury | Veteran's Stadium-Willow Brook Park - Football Field |
| THU 10/26 | 4:00 PM | League | Amity | Sheehan | Amity Regional High School - William Johnson Stadium Field |
| THU 10/26 | 4:00 PM | League | Darien | Greenwich | Darien High School - DHS Stadium East |
| THU 10/26 | 4:00 PM | League | New Milford | Joel Barlow | New Milford High School - North Turf Field - NMHS |
| THU 10/26 | 4:00 PM | League | North Haven | Shelton | North Haven Middle School - Vanacore Field |
| THU 10/26 | 4:30 PM | League | Fairfield Warde | Westhill | Fairfield Warde High School - Tetreau/Davis Field |
| THU 10/26 | 4:30 PM | League | Norwalk | Stamford | Nathan Hale MS - Callahan Complex at Nathan Hale Lower |
| THU 10/26 | 5:00 PM | League | Brien McMahon | Danbury | Brien McMahon High School - Casagrande Field |
| THU 10/26 | 5:00 PM | League | New Canaan | Wilton | New Canaan HS - Dunning Stadium |
| THU 10/26 | 5:00 PM | Non-League | Hillhouse | Fitch | Bowen Field - Football Field |
| THU 10/26 | 6:00 PM | League | Cheshire | Notre Dame-West Haven | Cheshire High Main Game field - Cheshire High Main Game field |
| THU 10/26 | 6:00 PM | League | Daniel Hand | Xavier | Daniel Hand High School - Turf Field |
| THU 10/26 | 6:00 PM | League | Masuk | Bethel | Masuk High School - Benedict Stadium Field @ Masuk HS |
| THU 10/26 | 6:00 PM | League | Staples | St. Joseph | Staples High School - Staples Stadium |
| THU 10/26 | 6:00 PM | League | Trumbull | Ridgefield | Trumbull High School - McDougall Stadium |
| THU 10/26 | 6:00 PM | League | West Haven | Newtown | West Haven High School - Ken Strong Stadium |
| THU 10/26 | Canceled | League | Northwest Catholic | Bristol Eastern | Northwest Catholic High School (Primary) - NWC Lacrosse Field |
| SAT 10/28 | 10:00 AM | Non-League | ATI | New Fairfield | Immaculate High School - Mustang Valley |
| SAT 10/28 | 11:00 AM | League | Crosby | Oxford | Crosby High School - CHS - Jimmy Lee Stadium (Turf) |
| SAT 10/28 | 12:30 PM | Non-League | Wilcox Tech | Northwest United | Wilcox Tech - Football Field |
| SAT 10/28 | 9:30 AM | League | Watertown | Woodland | Watertown High - John J Mills Complex @ Watertown HS |
| SAT 10/28 | Postponed | League | Wilby | Holy Cross | Wilby High School - Football Field |
| THU 11/2 | 3:45 PM | League | Conard | Glastonbury | Conard High School - Football Field - Grass |
| THU 11/2 | 3:45 PM | League | East Hartford | Hall | East Hartford High School - Freshman Practice Field |
| THU 11/2 | 3:45 PM | League | Enfield | Wethersfield | Enfield High School - EHS TURF |
| THU 11/2 | 3:45 PM | League | Farmington | Platt | Farmington High School - Turf Field |
| THU 11/2 | 3:45 PM | League | Newington | Berlin | Newington High School - Abbate Field, Alumni Rd. |
| THU 11/2 | 3:45 PM | League | Windsor | Manchester | Windsor High School - Jack O'Brien Stadium |
| THU 11/2 | 4:00 PM | League | Greenwich | Trumbull | Greenwich High School - Cardinal Stadium |
| THU 11/2 | 4:00 PM | League | Newtown | Pomperaug | Newtown High School - NHS Back Turf Field |
| THU 11/2 | 4:00 PM | League | Notre Dame-West Haven | West Haven | Veterans Memorial Park (West Haven, CT) - Field |
| THU 11/2 | 4:00 PM | League | Xavier | Fairfield Prep | Xavier High School - Larry McHugh Field |
| THU 11/2 | 4:30 PM | League | Wilton | St. Joseph | Wilton High School - Fuijitani Field -Turf |
| THU 11/2 | 5:00 PM | League | Danbury | Fairfield Ludlowe | Danbury High School - Stadium Turf Field |
| THU 11/2 | 5:00 PM | League | Foran | Lyman Hall | Foran High School - Foran High School - Turf Field |
| THU 11/2 | 5:00 PM | League | Stamford | Fairfield Warde | Stamford High School - Boyle Stadium |
| THU 11/2 | 5:30 PM | League | Hamden | Shelton | Hamden High School - HHS Turf #1 |
| THU 11/2 | 5:30 PM | League | Joel Barlow | New Fairfield | Joel Barlow High School - Field I (Stadium) |
| THU 11/2 | 5:30 PM | Non-League | E.O. Smith | Stafford, East Windsor, Somers | E.O. Smith High School - Turf Field |
| THU 11/2 | 5:45 PM | League | New Milford | Stratford | New Milford High School - North Turf Field - NMHS |
| THU 11/2 | 6:00 PM | League | Cheshire | North Haven | Cheshire High Main Game field - Cheshire High Main Game field |
| THU 11/2 | 6:00 PM | League | Daniel Hand | Amity | Daniel Hand High School - Turf Field |
| THU 11/2 | 6:00 PM | League | Simsbury | New Britain | Holden Field - Turf |
| THU 11/2 | 6:00 PM | League | Southington | Maloney | Southington High School - 3 TURF FIELD |
| THU 11/2 | 6:00 PM | League | Staples | Darien | Staples High School - Staples Stadium |
| THU 11/2 | 6:30 PM | League | Ridgefield | New Canaan | Ridgefield High School - Tiger Hollow Turf Field II |
| THU 11/2 | 6:30 PM | Non-League | Sheehan | Masuk | Sheehan High School - Sheehan HS Riccitelli Field (Turf) |
| THU 11/2 | Canceled | League | Hartford Public | Northwest Catholic | Hartford Public High School - Football Field |
| THU 11/2 | Canceled | League | Westhill | Brien McMahon | Westhill High School - J. Walter Kennedy Stadium |
| FRI 11/3 | 3:45 PM | League | Avon | South Windsor | Avon High School - Turf Field |
| SAT 11/4 | 10:00 AM | League | Watertown | Holy Cross | Watertown High - John J Mills Complex @ Watertown HS |
| SAT 11/4 | 11:00 AM | League | Crosby | Naugatuck | Crosby High School - CHS - Jimmy Lee Stadium (Turf) |
| SAT 11/4 | 9:30 AM | League | Bristol Central | Middletown | Bristol Central High School - BC Turf Field |
| TUE 11/7 | 5:00 PM | League | Wolcott | GNH | Wolcott High School - Turf Field |
| WED 11/8 | 6:00 PM | League | Newtown | Jonathan Law | Newtown High School - Blue and Gold Stadium |
| WED 11/8 | Canceled | League | Platt | E.O. Smith | Platt High School - Platt Turf field |
| THU 11/9 | 3:00 PM | League | South Windsor | Rocky Hill | South Windsor High School - Field in front of HS |
| THU 11/9 | 3:15 PM | League | Hall | Simsbury | Hall High School - Football Practice Field |
| THU 11/9 | 3:15 PM | League | Wethersfield | Manchester | Wethersfield High School - Cottone Field |
| THU 11/9 | 3:30 PM | League | Greenwich | Staples | Greenwich High School - Field 7 |
| THU 11/9 | 3:45 PM | League | Daniel Hand | Sheehan | Madison Surf Club - Strong Field |
| THU 11/9 | 3:45 PM | League | Maloney | Conard | Maloney High School - Turf Field |
| THU 11/9 | 3:45 PM | League | Middletown | Enfield | Middletown High School - MHS Stadium |
| THU 11/9 | 3:45 PM | League | New Britain | East Hartford | Osgood Park - Osgood Park |
| THU 11/9 | 4:00 PM | League | Fairfield Prep | West Haven | Fairfield University - Rafferty Stadium |
| THU 11/9 | 4:00 PM | League | Shelton | Xavier | Shelton High School - Finn Stadium |
| THU 11/9 | 4:30 PM | League | Glastonbury | Southington | Glastonbury High School - Turf Field |
| THU 11/9 | 4:45 PM | League | Bristol Central | Bristol Eastern | Bristol Central High School - BC Turf Field |
| THU 11/9 | 5:00 PM | League | Darien | Danbury | Darien High School - DHS Stadium Field |
| THU 11/9 | 5:00 PM | League | Fairfield Warde | Fairfield Ludlowe | Fairfield Warde High School - Tetreau/Davis Field |
| THU 11/9 | 5:00 PM | League | Stamford | Westhill | Stamford High School - Boyle Stadium |
| THU 11/9 | 5:00 PM | League | Windsor | Berlin | Windsor High School - Jack O'Brien Stadium |
| THU 11/9 | 5:30 PM | League | New Milford | Masuk | New Milford High School - North Turf Field - NMHS |
| THU 11/9 | 5:30 PM | League | Trumbull | St. Joseph | Trumbull High School - McDougall Stadium |
| THU 11/9 | 6:00 PM | League | Norwalk | Brien McMahon | Norwalk High School - Testa Field |
| THU 11/9 | 6:30 PM | League | Ridgefield | Wilton | Ridgefield High School - Tiger Hollow Stadium |
| THU 11/9 | Canceled | League | Farmington | Hartford Public | Farmington High School - Turf Field |
| FRI 11/10 | 3:00 PM | League | Oxford | Ansonia | Oxford High School - Wolverine Field |
| FRI 11/10 | 4:00 PM | League | Notre Dame-West Haven | Hamden | Veterans Memorial Park (West Haven, CT) - Field |
| SAT 11/11 | 10:00 AM | League | Bristol Eastern | Avon | Bristol Eastern High School - Alumni Field-Turf |
| SAT 11/11 | 10:00 AM | League | Torrington | Wilby | Torrington High School - Robert Frost Sports Complex |
| SAT 11/11 | 10:00 AM | Non-League | ATI | Brookfield | Immaculate High School - Mustang Valley |
| SAT 11/11 | 11:00 AM | League | Naugatuck | Seymour | Naugatuck High School - Veterans Field |
| SAT 11/11 | 11:00 AM | League | WCA | Crosby | Waterbury Career Academy - Football Field |
| SAT 11/11 | Canceled | League | Watertown | Wolcott | Watertown High - John J Mills Complex @ Watertown HS |
| TUE 11/14 | 3:45 PM | League | Maloney | Platt | Falcon Field (Meriden, CT) - Football Field |
| TUE 11/14 | 4:00 PM | League | Pomperaug | Joel Barlow | Pomperaug High School - Stadium |
| WED 11/15 | 3:45 PM | League | Newington | Wethersfield | Clem Lemire Complex - Football Field |
| WED 11/15 | 4:00 PM | League | North Haven | Hamden | North Haven Middle School - Vanacore Field |
| WED 11/15 | 5:00 PM | League | Crosby | Kennedy | Crosby High School - CHS - Jimmy Lee Stadium (Turf) |
| THU 11/16 | 3:00 PM | League | South Windsor | Enfield | South Windsor High School - Field in front of HS |
| THU 11/16 | 3:15 PM | Non-League | Platt Tech | Amity | Orange Ave. Athletic Complex - Football Field |
| THU 11/16 | 3:45 PM | League | East Hartford | Manchester | East Hartford High School - Freshman Practice Field |
| THU 11/16 | 3:45 PM | League | Glastonbury | Simsbury | Glastonbury High School - Turf Field |
| THU 11/16 | 4:00 PM | League | Fairfield Prep | Notre Dame-West Haven | Fairfield University - Rafferty Stadium |
| THU 11/16 | 4:00 PM | League | Hall | Conard | Hall High School - Stadium (Turf Field) |
| THU 11/16 | 4:30 PM | League | Wilton | Shelton | Wilton High School - Fuijitani Field -Turf |
| THU 11/16 | 5:00 PM | League | Danbury | Ridgefield | Danbury High School - Stadium Turf Field |
| THU 11/16 | 5:00 PM | League | Middletown | Berlin | Middletown High School - MHS Stadium |
| THU 11/16 | 5:00 PM | League | Naugatuck | Ansonia | Naugatuck High School - Veterans Field |
| THU 11/16 | 5:00 PM | League | New Canaan | Darien | New Canaan HS - Dunning Stadium |
| THU 11/16 | 5:00 PM | League | Watertown | Torrington | Watertown High - John J Mills Complex @ Watertown HS |
| THU 11/16 | 5:00 PM | Scrimmage | Fairfield Warde | East Haven | Fairfield Warde High School - Tetreau/Davis Field |
| THU 11/16 | 5:15 PM | League | Windsor | Avon | Windsor High School - Jack O'Brien Stadium |
| THU 11/16 | 6:00 PM | League | Masuk | Newtown | Masuk High School - Benedict Stadium Field @ Masuk HS |
| THU 11/16 | 6:00 PM | League | West Haven | Cheshire | West Haven High School - Ken Strong Stadium |
| THU 11/16 | Canceled | League | Hartford Public | New Britain | Hartford Public High School - Football Field |
| THU 11/16 | Canceled | League | New Milford | New Fairfield | New Milford High School - North Turf Field - NMHS |
| THU 11/16 | Canceled | League | Wilbur Cross | Xavier | Wilbur Cross High School - Wilbur Cross Athletic Complex |
| THU 11/16 | Canceled | Non-League | Fairfield Warde | East Haven | Fairfield Warde High School - Tetreau/Davis Field |
| THU 11/16 | Canceled | Non-League | Rockville | E.O. Smith | Rockville High School - Stadium Field |
| FRI 11/17 | 4:00 PM | League | Stratford | Bunnell | Penders Field - Penders Field - Stratford |
| FRI 11/17 | 6:00 PM | League | Southington | Xavier | Southington High School - 3 TURF FIELD |
| SAT 11/18 | 10:30 AM | League | Hillhouse | Wilbur Cross | Wilbur Cross High School - Wilbur Cross Athletic Complex |
| SAT 11/18 | 5:00 PM | League | Wolcott | Holy Cross | Wolcott High School - Turf Field |
| MON 11/20 | 5:30 PM | League | Pomperaug | New Milford | Pomperaug High School - Stadium |
| TUE 11/21 | 5:00 PM | Scrimmage | Maloney | Platt | Maloney High School - Falcon Field |