| GameDate | Time | Type | Home School | Away School | Site |
| 09/04/2026 | 5:00 PM | League | Pomperaug | Bethel, Cheshire, Notre Dame-West Haven, Naugatuck | Pomperaug High School - Track |
| 09/08/2026 | 3:45 PM | League | Kaynor Tech | Wolcott Tech | Black Rock State Park - Black Rock State Park |
| 09/08/2026 | 3:45 PM | League | Bloomfield | Hall, Farmington, Central Connecticut Conference (CCC) | Bloomfield High School - Cross Country Course |
| 09/08/2026 | 3:45 PM | League | Central Connecticut Conference (CCC) | Lewis Mills, Bristol Eastern, Avon, Bristol Central | Bristol Eastern High School - Page Park |
| 09/08/2026 | 3:45 PM | League | Platt Tech | Wilcox Tech | Eisenhower Park - Eisenhower |
| 09/08/2026 | 3:45 PM | League | Aerospace | Achievement First, Capital Prep, Comp Sci, International, Hartford Public, Classical Magnet, Bulkeley, University, Weaver, SMSA, HMTCA, Parish Hill, Innovation | Elizabeth Park - Cross Country Course |
| 09/08/2026 | 3:45 PM | League | Enfield | Central Connecticut Conference (CCC), East Catholic, East Hartford | Enfield High School - Cross Country Course |
| 09/08/2026 | 3:45 PM | League | Newington | Plainville, New Britain, Platt, Central Connecticut Conference (CCC) | John Wallace MS - John Wallace MS |
| 09/08/2026 | 3:45 PM | League | E.O. Smith | RHAM, Central Connecticut Conference (CCC), Glastonbury | Mansfield Hollow State Park - Girls Course |
| 09/08/2026 | 3:45 PM | League | Norwich Tech | Vinal Tech | Norwich Technical High School - Mohegan Park |
| 09/08/2026 | 3:45 PM | League | Berlin | Maloney, Middletown, Central Connecticut Conference (CCC) | Pistol Creek - Pistol Creek |
| 09/08/2026 | 3:45 PM | League | Southington | Central Connecticut Conference (CCC), Rocky Hill, Wethersfield | Southington High School - Sloper |
| 09/08/2026 | 3:45 PM | League | Simsbury | Northwest Catholic, Conard, Central Connecticut Conference (CCC) | Stratton Brook State Park - Stratton Brook State Park |
| 09/08/2026 | 3:45 PM | League | Manchester | Central Connecticut Conference (CCC), South Windsor, Tolland, Windsor | Wickham Park - Wickham Park |
| 09/08/2026 | 4:00 PM | League | Wilbur Cross | Cheshire, Guilford, Mercy | East Rock Park - East Rock Park |
| 09/08/2026 | 4:15 PM | League | Abbott Tech | Wright Tech | Wooster Cemetary - Wooster Cemetary |
| 09/09/2026 | 3:45 PM | League | Foran | Hamden, Career Magnet, Shelton | Eisenhower Park - EISENHOWER PARK |
| 09/09/2026 | 4:00 PM | League | East Haven | Lauralton Hall, Lyman Hall, Jonathan Law | East Haven High School - EHHS Turf Field & Track |
| 09/09/2026 | 4:00 PM | League | Somers | Stafford | Somers High School - P&R Fields |
| 09/09/2026 | 4:00 PM | League | Canton | East Granby, Coventry, Ellington | Stratton Brook State Park - Stratton Brook State Park |
| 09/09/2026 | 4:15 PM | League | Bolton | Rockville | Bolton High School - BHS Cross Country Course |
| 09/09/2026 | 4:15 PM | League | Windsor Locks | Suffield, East Windsor, Granby Memorial | Windsor Locks High School - Track |
| 09/11/2026 | 3:30 PM | Non-League | Middletown | | Veterans Memorial Park, Middletown, CT - Veterans Memorial Park, Middletown, CT |
| 09/15/2026 | 3:30 PM | League | Naugatuck | Kennedy, WCA | Hop Brook Park - Hop Brook Park |
| 09/15/2026 | 3:30 PM | League | Wolcott | Wilby, St. Paul Catholic, Derby EOB | Wolcott High School - WHS Track and Lower Field |
| 09/15/2026 | 3:45 PM | League | Crosby | Seymour, Woodland, Watertown | Bucks Hill (MONTOE) Park - Soccer Pitch |
| 09/15/2026 | 3:45 PM | League | Aerospace | University, Weaver, SMSA, HMTCA, Parish Hill, Innovation, International, Comp Sci, Bulkeley, Classical Magnet, Hartford Public, Achievement First, Capital Prep | Colt Park - Cross Country Course |
| 09/15/2026 | 3:45 PM | League | Platt Tech | Kaynor Tech | Eisenhower Park - Eisenhower |
| 09/15/2026 | 3:45 PM | League | Avon | Central Connecticut Conference (CCC), Farmington, Northwest Catholic | Fisher Meadow Soccer Fields - Avon High School-Fisher Meadows at Avon Old Farms |
| 09/15/2026 | 3:45 PM | League | Grasso Tech | Windham Tech | Grasso Tech - Haley Farm |
| 09/15/2026 | 3:45 PM | League | Hall | Simsbury, Bristol Eastern, Central Connecticut Conference (CCC) | Hall High School - Stadium (Track) |
| 09/15/2026 | 3:45 PM | League | Holy Cross | Oxford, Torrington | Holy Cross - Holy Cross |
| 09/15/2026 | 3:45 PM | League | Maloney | Newington, Central Connecticut Conference (CCC), Wethersfield | Hubbard Park - Hubbard Park Band Shell |
| 09/15/2026 | 3:45 PM | League | Wilcox Tech | Wright Tech, Bullard Havens Tech | Hubbard Park - Hubbard Park Band Shell |
| 09/15/2026 | 3:45 PM | League | Lewis Mills | Bristol Central, Bloomfield, Conard | Johnnycake Mountain Park - Johnnycake Mountain Park |
| 09/15/2026 | 3:45 PM | League | Nonnewaug | Northwestern, Housatonic Regional | Nonnewaug High School - XC Course |
| 09/15/2026 | 3:45 PM | League | Norwich Tech | Ellis Tech | Norwich Technical High School - Mohegan Park |
| 09/15/2026 | 3:45 PM | League | Plainville | Berlin, Rocky Hill, Central Connecticut Conference (CCC) | Plainville High School - Cross Country Course |
| 09/15/2026 | 3:45 PM | League | Plainville | Rocky Hill, Berlin | Plainville High School - Cross Country Course -Middle School of Plainville |
| 09/15/2026 | 3:45 PM | League | New Britain | Middletown, Platt, Southington, Central Connecticut Conference (CCC) | Stanley Quarter Park - Cross Country |
| 09/15/2026 | 3:45 PM | League | Tolland | Central Connecticut Conference (CCC), Enfield, E.O. Smith | Tolland High School - Grass Field |
| 09/15/2026 | 3:45 PM | League | Vinal Tech | Prince Tech, Cheney Tech | Vinal Tech - Vinal CC Course |
| 09/15/2026 | 3:45 PM | League | East Hartford | Glastonbury, Central Connecticut Conference (CCC), South Windsor | Wickham Park - Wickham Park |
| 09/15/2026 | 3:45 PM | League | Windsor | Manchester, East Catholic, RHAM, Central Connecticut Conference (CCC) | Windsor High School - Northwest Park |
| 09/15/2026 | 4:00 PM | League | Darien | Danbury, Bridgeport Central, Wilton | Darien High School - DHS Stadium East |
| 09/15/2026 | 4:00 PM | League | Ledyard | Tourtellotte, Plainfield, East Lyme, Killingly | Ledyard High School - Ledyard High School Track |
| 09/15/2026 | 4:00 PM | League | Montville | Lyman Memorial, Bacon Academy, Putnam, Wheeler | Montville High School - XC Course |
| 09/15/2026 | 4:00 PM | League | Ridgefield | Westhill, St. Joseph, Fairfield Warde | Ridgefield High School - Upper Grass Field |
| 09/15/2026 | 4:00 PM | League | Shepaug Valley | Gilbert, ACES at Chase | Shepaug Valley High School - Shepaug Valley Middle & High School Cross Country Course |
| 09/15/2026 | 4:30 PM | League | Brookfield | New Milford, Newtown, Stratford | Brookfield High School - BHS Track |
| 09/15/2026 | 4:30 PM | League | NFA | Stonington, Waterford, Woodstock Academy | Mohegan Park - Mohegan Park |
| 09/15/2026 | 4:30 PM | League | Kolbe Cathedral | Bethel, Immaculate, Joel Barlow | Seaside Park - Seaside Park |
| 09/15/2026 | 4:30 PM | League | Harding | Notre Dame Prep, Bassick, New Fairfield | Warren Harding High School - Beardsley Park |
| 09/15/2026 | 4:30 PM | League | New Canaan | Staples, Norwalk, Fairfield Ludlowe | Waveny Park - Waveny Park |
| 09/15/2026 | 5:00 PM | League | Trumbull | Brien McMahon, Greenwich, Stamford | Trumbull High School - Cross Country Course |
| 09/16/2026 | 3:45 PM | League | East Windsor | Somers, Rockville, Ellington | East Windsor Resevoir - East Windsor Resevoir |
| 09/16/2026 | 3:45 PM | League | Canton | Windsor Locks | Stratton Brook State Park - Stratton Brook State Park |
| 09/16/2026 | 4:00 PM | Tournament | Sheehan | | Sheehan High School - Sheehan HS Cross Country Course |
| 09/17/2026 | 3:30 PM | Non-League | Coginchaug | | Coginchaug Regional High School - Coginchaug Regional HS |
| 09/22/2026 | 3:30 PM | League | Wolcott | Holy Cross, WCA, Seymour | Wolcott High School - WHS Track and Lower Field |
| 09/22/2026 | 3:45 PM | League | Crosby | Wilby, Oxford | Bucks Hill (MONTOE) Park - Soccer Pitch |
| 09/22/2026 | 3:45 PM | League | Platt Tech | Wolcott Tech | Eisenhower Park - Eisenhower |
| 09/22/2026 | 3:45 PM | League | Grasso Tech | Norwich Tech | Grasso Tech - Haley Farm |
| 09/22/2026 | 3:45 PM | League | Morgan | Old Saybrook, Lyme-Old Lyme, Valley Regional | Indian River Complex - XC Course |
| 09/22/2026 | 3:45 PM | League | Wright Tech | Kaynor Tech | Scalzi Park - Scalzi Park |
| 09/22/2026 | 3:45 PM | League | Aerospace | Weaver, University, SMSA, HMTCA, Innovation, Parish Hill, Comp Sci, International, Bulkeley, Hartford Public, Classical Magnet, Achievement First, Capital Prep | Stanley Quarter Park - Cross Country |
| 09/22/2026 | 3:45 PM | League | Torrington | Kennedy, St. Paul Catholic, Woodland | Torrington High School - THS Cross Country Course |
| 09/22/2026 | 3:45 PM | League | Vinal Tech | Ellis Tech | Vinal Tech - Vinal CC Course |
| 09/22/2026 | 3:45 PM | League | Watertown | Derby EOB, Naugatuck | Watertown High School - Veteran's Park |
| 09/22/2026 | 4:00 PM | League | Wilton | Fairfield Warde, Brien McMahon, Norwalk | Allen's Meadow - XC Course |
| 09/22/2026 | 4:00 PM | League | Waterford | Lyman Memorial | Harkness State Park - Harkness State Park |
| 09/22/2026 | 4:00 PM | League | Mercy | Jonathan Law, Branford, Amity | Mercy High School - Cross Country Course |
| 09/22/2026 | 4:00 PM | League | Killingly | New London, Montville | Owen Bell Park - Owen Bell Track |
| 09/22/2026 | 4:00 PM | League | Westhill | Staples, Darien, Greenwich | Scofield Magnet Middle School - Cross Country Course |
| 09/22/2026 | 4:00 PM | League | St. Joseph | Fairfield Ludlowe, Bridgeport Central, Stamford | St. Joseph High School - Trail |
| 09/22/2026 | 4:00 PM | League | Danbury | Trumbull, Ridgefield, New Canaan | Tarrywile Park - Tarrywile Park |
| 09/22/2026 | 4:15 PM | League | Abbott Tech | Wilcox Tech, Bullard Havens Tech | Wooster Cemetary - Wooster Cemetary |
| 09/22/2026 | 4:30 PM | League | Masuk | Bethel, Bassick, Newtown | Great Hollow Lake Field - Cross Country Trail |
| 09/22/2026 | 4:30 PM | League | Fitch | NFA | Haley Farm State Park - Haley Farm State Park |
| 09/22/2026 | 4:30 PM | League | Joel Barlow | Harding, Brookfield, Bunnell | Joel Barlow High School - Cross Country Course |
| 09/22/2026 | 4:30 PM | League | Pomperaug | Immaculate, Stratford, New Fairfield | Settlers Park - Cross Country Course |
| 09/22/2026 | 4:30 PM | League | Weston | New Milford, Notre Dame Prep, Kolbe Cathedral | Weston High School - WHS Track |
| 09/22/2026 | 4:30 PM | League | Wheeler | Tourtellotte, Windham | Wheeler Middle High School - MHS XC Course |
| 09/22/2026 | 5:15 PM | League | St. Bernard | Plainfield, Putnam, Stonington, Griswold | St. Bernard School - Track |
| 09/23/2026 | 3:45 PM | League | Granby Memorial | Canton, Rockville | Granby Memorial High School - XC Course |
| 09/23/2026 | 4:00 PM | League | Suffield | Stafford, Ellington | Suffield High School - Bruce Park |
| 09/23/2026 | 4:15 PM | League | Bolton | Coventry, Windsor Locks, Somers | Bolton High School - BHS Cross Country Course |
| 09/29/2026 | 3:30 PM | League | Hale Ray | Portland, Lyme-Old Lyme, Coginchaug, Old Saybrook | Nathan Hale Ray High School - HS XC Course |
| 09/29/2026 | 3:45 PM | League | Central Connecticut Conference (CCC) | Lewis Mills, Bristol Central, Northwest Catholic, Hall | Bristol Central High School - Rockwell Park |
| 09/29/2026 | 3:45 PM | League | Rocky Hill | Platt, Maloney, New Britain | Elm Ridge Park - Elm Ridge Park |
| 09/29/2026 | 3:45 PM | League | Simsbury | Avon, Bloomfield, Central Connecticut Conference (CCC) | Fisher Meadow - Avon |
| 09/29/2026 | 3:45 PM | League | Grasso Tech | Ellis Tech | Grasso Tech - Haley Farm |
| 09/29/2026 | 3:45 PM | League | Wilcox Tech | Wolcott Tech | Hubbard Park - Hubbard Park Band Shell |
| 09/29/2026 | 3:45 PM | League | Glastonbury | Manchester, Windsor, Central Connecticut Conference (CCC), Enfield | JB Williams Park - JB Williams Park |
| 09/29/2026 | 3:45 PM | League | Derby EOB | Torrington, Seymour | Leo F. Ryan Athletic Complex - Lou Defilippo Field |
| 09/29/2026 | 3:45 PM | League | Aerospace | Parish Hill, Innovation, HMTCA, SMSA, University, Weaver, Capital Prep, Achievement First, International, Comp Sci, Classical Magnet, Hartford Public, Bulkeley | Northwest Park - Cross Country Course |
| 09/29/2026 | 3:45 PM | League | Berlin | Southington, Newington, Central Connecticut Conference (CCC) | Pistol Creek - Pistol Creek |
| 09/29/2026 | 3:45 PM | League | Conard | Central Connecticut Conference (CCC), Farmington, Bristol Eastern | Reservoir Rt. 4 - Reservoir Rt. 4 |
| 09/29/2026 | 3:45 PM | League | RHAM | East Hartford, Tolland, Central Connecticut Conference (CCC) | RHAM High School - MS Baseball/Soccer Field |
| 09/29/2026 | 3:45 PM | League | Wright Tech | Platt Tech | Scalzi Park - Scalzi Park |
| 09/29/2026 | 3:45 PM | League | Watertown | Wolcott, Kennedy, Oxford | Watertown High School - Veteran's Park |
| 09/29/2026 | 3:45 PM | League | Wethersfield | Plainville, Middletown, Central Connecticut Conference (CCC) | Wethersfield Cove Park - Wethersfield Cove Park |
| 09/29/2026 | 3:45 PM | League | East Catholic | Central Connecticut Conference (CCC), South Windsor, E.O. Smith | Wickham Park - Wickham Park |
| 09/29/2026 | 3:45 PM | League | Woodland | Naugatuck, Holy Cross, Wilby | Woodland High School - Track |
| 09/29/2026 | 3:45 PM | Non-League | Jonathan Law | Platt Tech, Foran, Lauralton Hall | Eisenhower Park - Eisenhower Park |
| 09/29/2026 | 4:00 PM | League | WCA | Crosby, St. Paul Catholic | Bucks Hill (MONTOE) Park - XC Course |
| 09/29/2026 | 4:00 PM | League | Griswold | Bacon Academy | Griswold High School - Hopeville State Park |
| 09/29/2026 | 4:00 PM | League | Housatonic Regional | Gilbert, Terryville | Housatonic Valley Regional High - Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) |
| 09/29/2026 | 4:00 PM | League | Westhill | Trumbull, Wilton, Fairfield Ludlowe | Scofield Magnet Middle School - Cross Country Course |
| 09/29/2026 | 4:00 PM | League | Staples | Danbury, Brien McMahon, St. Joseph | Staples High School - Staples Stadium |
| 09/29/2026 | 4:00 PM | League | Thomaston | Nonnewaug, ACES at Chase | Thomaston High School - Black Rock State Park |
| 09/29/2026 | 4:00 PM | League | New Canaan | Stamford, Darien, Fairfield Warde | Waveny Park - Waveny Park |
| 09/29/2026 | 4:15 PM | League | Abbott Tech | Kaynor Tech | Wooster Cemetary - Wooster Cemetary |
| 09/29/2026 | 4:30 PM | League | Bethel | Bunnell, Notre Dame Prep, Stratford | Bethel High School - Track |
| 09/29/2026 | 4:30 PM | League | Fitch | East Lyme | Haley Farm State Park - Haley Farm State Park |
| 09/29/2026 | 4:30 PM | League | Immaculate | Harding, Newtown, Weston | Immaculate High School - Immaculate HS |
| 09/29/2026 | 4:30 PM | League | NFA | Ledyard | Mohegan Park - Mohegan Park |
| 09/29/2026 | 4:30 PM | League | New Fairfield | Joel Barlow, New Milford, Masuk | New Fairfield High School - Track & Field, Cross Country |
| 09/29/2026 | 4:30 PM | League | Stonington | Lyman Memorial | Stonington High School - Palmer Field (Turf Stadium) |
| 09/30/2026 | 3:45 PM | League | Granby Memorial | East Granby, Somers | Granby Memorial High School - XC Course |
| 09/30/2026 | 4:00 PM | League | Ellington | Windsor Locks | Ellington High School - Track |
| 09/30/2026 | 4:00 PM | League | Ridgefield | Norwalk, Greenwich, Bridgeport Central | Ridgefield High School - Upper Grass Field |
| 09/30/2026 | 4:00 PM | League | Suffield | Rockville | Suffield High School - Bruce Park |
| 09/30/2026 | 4:15 PM | League | Stafford | Canton, Bolton, East Windsor | Stafford High School - Stafford High School |
| 10/02/2026 | 3:45 PM | Non-League | Nonnewaug | | Nonnewaug High School - XC Course |
| 10/06/2026 | 3:45 PM | League | Kaynor Tech | Wilcox Tech | Black Rock State Park - Black Rock State Park |
| 10/06/2026 | 3:45 PM | League | WCA | Watertown, Wilby, Torrington | Bucks Hill (MONTOE) Park - XC Course |
| 10/06/2026 | 3:45 PM | League | Aerospace | HMTCA, SMSA, University, Weaver, Parish Hill, Innovation, Achievement First, Capital Prep, Bulkeley, Hartford Public, Classical Magnet, International, Comp Sci | Elizabeth Park - Cross Country Course |
| 10/06/2026 | 3:45 PM | League | Holy Cross | Derby EOB, Kennedy, Crosby | Holy Cross - Holy Cross |
| 10/06/2026 | 3:45 PM | League | Platt | Berlin, New Britain, Wethersfield, Central Connecticut Conference (CCC) | Hubbard Park - Tennis courts |
| 10/06/2026 | 3:45 PM | League | Glastonbury | Central Connecticut Conference (CCC), Tolland, East Catholic | JB Williams Park - JB Williams Park |
| 10/06/2026 | 3:45 PM | League | South Windsor | Enfield, RHAM | Nevers Road Park - Nevers Road Park XC Trail |
| 10/06/2026 | 3:45 PM | League | Bristol Eastern | Northwest Catholic, Bloomfield, Central Connecticut Conference (CCC) | Page Park Bristol CT - Cross Country |
| 10/06/2026 | 3:45 PM | League | Conard | Central Connecticut Conference (CCC), Avon, Hall | Reservoir Rt. 4 - Reservoir Rt. 4 |
| 10/06/2026 | 3:45 PM | League | Southington | Plainville, Maloney, Central Connecticut Conference (CCC) | Southington High School - Sloper |
| 10/06/2026 | 3:45 PM | League | St. Paul Catholic | Seymour, Naugatuck, Oxford | St. Paul Catholic HS - SP Track |
| 10/06/2026 | 3:45 PM | League | Middletown | Rocky Hill, Newington, Central Connecticut Conference (CCC) | Veterans Memorial Park, Middletown, CT - Veterans Memorial Park, Middletown, CT |
| 10/06/2026 | 3:45 PM | League | East Hartford | Manchester, Windsor, Central Connecticut Conference (CCC), E.O. Smith | Wickham Park - Wickham Park |
| 10/06/2026 | 3:45 PM | League | Woodland | Wolcott | Woodland High School - Track |
| 10/06/2026 | 4:00 PM | League | Housatonic Regional | Shepaug Valley, Thomaston | Housatonic Valley Regional High - Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) |
| 10/06/2026 | 4:00 PM | League | Lakeview | Nonnewaug, Gilbert | LHS - 2B |
| 10/06/2026 | 4:00 PM | League | Lyman Memorial | Griswold | Lyman Memorial High School - Track |
| 10/06/2026 | 4:00 PM | League | Plainfield | Fitch, Ledyard, New London, Wheeler | Plainfield High School Athletic Upper Complex - Cross Country Course |
| 10/06/2026 | 4:00 PM | League | Putnam | Windham, Killingly | St. Marie Greenhalgh Sports Complex - Nature Trail |
| 10/06/2026 | 4:00 PM | League | Fairfield Ludlowe | Fairfield Warde, Greenwich, Danbury | TBA - TBA |
| 10/06/2026 | 4:00 PM | League | Vinal Tech | Grasso Tech | Vinal Tech - Vinal CC Course |
| 10/06/2026 | 4:00 PM | League | New Canaan | Bridgeport Central, Brien McMahon, Westhill | Waveny Park - Waveny Park |
| 10/06/2026 | 4:15 PM | League | Wilton | Stamford, Staples, Ridgefield | Allen's Meadow - XC Course |
| 10/06/2026 | 4:15 PM | League | Abbott Tech | Platt Tech | Wooster Cemetary - Wooster Cemetary |
| 10/06/2026 | 4:30 PM | League | Masuk | Harding, Stratford, Kolbe Cathedral | Great Hollow Lake Field - Cross Country Trail |
| 10/06/2026 | 4:30 PM | League | East Lyme | Woodstock Academy | Rocky Neck State Park - Rocky Neck State Park |
| 10/06/2026 | 4:30 PM | League | Trumbull | St. Joseph, Norwalk, Darien | Trumbull High School - Cross Country Course |
| 10/06/2026 | 4:30 PM | League | Weston | Bethel, Brookfield, New Fairfield | Weston High School - WHS Track |
| 10/06/2026 | 4:30 PM | League | Farmington | Simsbury, Lewis Mills, Bristol Central | Winding Trails - Cross Country Course |
| 10/06/2026 | 5:00 PM | League | Newtown | Joel Barlow, Notre Dame Prep, Pomperaug | Fairfield Hills - Fairfield Hills |
| 10/07/2026 | 3:45 PM | League | Rockville | Windsor Locks, Stafford, East Granby | Rockville High School - Rockville Track |
| 10/07/2026 | 4:00 PM | League | Ellington | Granby Memorial, Bolton | Ellington High School - Track |
| 10/07/2026 | 4:00 PM | League | Somers | Canton, Suffield | Somers High School - P&R Fields |
| 10/12/2026 | 3:45 PM | League | Jonathan Law | Career Magnet, Cheshire | Eisenhower Park - Eisenhower Park |
| 10/13/2026 | 3:45 PM | League | ACES at Chase | Lakeview, Housatonic Regional | Aces Chase Academy - Baseball Diamond |
| 10/13/2026 | 3:45 PM | League | Derby EOB | Oxford, Woodland, WCA | Leo F. Ryan Athletic Complex - Lou Defilippo Field |
| 10/13/2026 | 3:45 PM | League | Aerospace | Parish Hill, Innovation, SMSA, HMTCA, Weaver, University, Comp Sci, International, Bulkeley, Classical Magnet, Hartford Public, Achievement First, Capital Prep | Northwest Park - Cross Country Course |
| 10/13/2026 | 3:45 PM | League | Seymour | Kennedy, Wilby | Seymour High School - Seymour High Lower Field |
| 10/13/2026 | 3:45 PM | League | Torrington | Wolcott, Crosby, Naugatuck | Torrington High School - THS Cross Country Course |
| 10/13/2026 | 3:45 PM | League | Watertown | Holy Cross, St. Paul Catholic | Watertown High School - Veteran's Park |
| 10/13/2026 | 3:45 PM | Non-League | Wilcox Tech | Maloney, Platt | Hubbard Park - Cross Country Course |
| 10/13/2026 | 3:45 PM | Non-League | Middletown | Lewis Mills | Veterans Memorial Park, Middletown, CT - Veterans Memorial Park, Middletown, CT |
| 10/13/2026 | 4:00 PM | League | Darien | Fairfield Ludlowe, Brien McMahon, Ridgefield | Darien High School - DHS Stadium East |
| 10/13/2026 | 4:00 PM | League | Gilbert | Thomaston, Northwestern | Gilbert School - Cross Country |
| 10/13/2026 | 4:00 PM | League | Ledyard | Lyman Memorial | Ledyard High School - Ledyard High School Track |
| 10/13/2026 | 4:00 PM | League | Killingly | St. Bernard, Wheeler | Owen Bell Park - Owen Bell Track |
| 10/13/2026 | 4:00 PM | League | Shepaug Valley | Nonnewaug, Terryville | Shepaug Valley High School - Shepaug Valley Middle & High School Cross Country Course |
| 10/13/2026 | 4:00 PM | League | Staples | Trumbull, Bridgeport Central, Fairfield Warde | Staples High School - Staples Stadium |
| 10/13/2026 | 4:00 PM | League | Danbury | Norwalk, Stamford, Westhill | Tarrywile Park - Tarrywile Park |
| 10/13/2026 | 4:00 PM | League | Windham | Plainfield, Montville | Windham High School - XC Course |
| 10/13/2026 | 4:00 PM | League | Woodstock Academy | Fitch, Griswold, Waterford | Woodstock Fairgrounds - Woodstock Fairgrounds |
| 10/13/2026 | 4:30 PM | League | Brookfield | Masuk, Immaculate, Notre Dame Prep | Brookfield High School - BHS Track |
| 10/13/2026 | 4:30 PM | League | NFA | East Lyme | Mohegan Park - Mohegan Park |
| 10/13/2026 | 4:30 PM | League | New Fairfield | Kolbe Cathedral, Bunnell, Newtown | New Fairfield High School - Track & Field, Cross Country |
| 10/13/2026 | 4:30 PM | League | New Milford | Harding, Pomperaug, Bethel | New Milford High School - Joe Wiser Stadium - NMHS |
| 10/13/2026 | 4:30 PM | League | Stratford | Bassick, Joel Barlow, Weston | Wooster Middle School Field - Wooster Middle School Field |
| 10/13/2026 | 4:30 PM | League | Bacon Academy | Tourtellotte, Putnam, Stonington, New London | Zagray Farm - Zagray Farm |
| 10/14/2026 | 4:00 PM | League | Guilford | Shelton, Branford, Lauralton Hall | Guilford High School - East River Preserve |
| 10/15/2026 | 3:45 PM | League | Amity | East Haven, Hamden, Hillhouse | Fitzgerald Field - Fitzgerald Field |
| 10/15/2026 | 4:30 PM | League | Bristol Central | Bristol Eastern | Rockwell Park - Cross Country Course |
| 10/20/2026 | 2:00 PM | League | Aerospace | Achievement First, Capital Prep, Hartford Public, Classical Magnet, Bulkeley, International, Comp Sci, Innovation, Parish Hill, Weaver, University, HMTCA, SMSA | Stanley Quarter Park - Cross Country |
| 10/20/2026 | 3:00 PM | Postseason | Central Connecticut Conference (CCC) | Tolland, Hall, Simsbury, Southington, South Windsor, Wethersfield, Plainville, Windsor, Rocky Hill, Manchester, Glastonbury, New Britain, Middletown, Platt, Maloney, Newington, Northwest Catholic, RHAM, Farmington, East Catholic, Lewis Mills, Enfield, E.O. Smith, East Hartford, Bristol Eastern, Bristol Central, Conard, Bloomfield, Avon, Berlin | Wickham Park - Wickham Park |
| 10/20/2026 | 3:45 PM | League | East Catholic | | Wickham Park - Wickham Park |
| 10/21/2026 | 2:00 PM | League | New Canaan | Brien McMahon, Bridgeport Central, Darien, Danbury, Fairfield Warde, Fairfield Ludlowe, Greenwich, St. Joseph, Ridgefield, Staples, Trumbull, Norwalk, Stamford, Wilton, Westhill | Waveny Park - Waveny Park |
| 10/21/2026 | 3:00 PM | League | Bolton | | Bolton High School - BHS Cross Country Course |
| 10/21/2026 | 3:30 PM | Postseason | Bethel | Bassick, Brookfield, Kolbe Cathedral, Bunnell, Joel Barlow, Immaculate, Notre Dame Prep, New Fairfield, Weston, Pomperaug, Stratford, Harding, Newtown, Masuk | Bethel High School - BHS track |
| 10/21/2026 | 3:30 PM | Postseason | St. Paul Catholic | Seymour, Watertown, Wolcott, WCA, Woodland, Torrington, Wilby, Naugatuck, Oxford, Derby EOB, Kennedy, Crosby, Holy Cross, Ansonia | Veterans Memorial Park - Veterans Park XC Course |
| 10/22/2026 | 2:30 PM | Postseason | Thomaston | Lakeview, Housatonic Regional, Shepaug Valley, Nonnewaug, Northwestern, Terryville, Gilbert, ACES at Chase | Thomaston High School - Black Rock State Park |