| Date | Time | Type | Home School | Away School | Site |
| SAT 9/6 | 10:00 AM | Non-League | Greenwich | Ramapo High School | Greenwich High School - Cardinal Stadium |
| WED 9/10 | 3:30 PM | League | Pomperaug | Ansonia | Pomperaug High School - Stadium |
| WED 9/10 | 3:45 PM | League | Newington | Bristol Central | Newington High School - Abbate Field, Alumni Rd. |
| WED 9/10 | 3:45 PM | League | Berlin | Wethersfield | Sage Park Berlin - Scalise Field |
| WED 9/10 | 4:00 PM | Non-League | Amity | Maloney | Amity Regional High School - William Johnson Stadium Field |
| WED 9/10 | Canceled | Non-League | Sheehan | | Sheehan High School - Sheehan HS Riccitelli Field (Turf) |
| THU 9/11 | 3:00 PM | Non-League | Conard | Shelton | Conard High School - Football Field - Grass |
| THU 9/11 | 3:45 PM | League | Hall | East Hartford | Hall High School - Football Practice Field |
| THU 9/11 | 4:00 PM | Non-League | Notre Dame-West Haven | Fairfield Ludlowe | Veterans Memorial Park (West Haven, CT) - Field |
| THU 9/11 | 4:30 PM | League | Greenwich | Fairfield Prep | Greenwich High School - GHS Field 7 |
| THU 9/11 | 4:30 PM | League | West Haven | Manchester | West Haven High School - Ken Strong Stadium |
| THU 9/11 | 5:00 PM | League | Cheshire | Xavier | Cheshire High School - Alumni Field - Turf |
| THU 9/11 | 5:00 PM | League | Stamford | Harding | Stamford High School - Boyle Stadium |
| THU 9/11 | 5:30 PM | League | Joel Barlow | Stratford | Joel Barlow High School - Field I (Stadium) |
| THU 9/11 | 5:30 PM | League | Norwalk | Darien | Nathan Hale Middle School - Callahan Complex at Nathan Hale Lower |
| THU 9/11 | 6:00 PM | League | Simsbury | E.O. Smith | Holden Field - Turf |
| THU 9/11 | 6:00 PM | Non-League | Danbury | Masuk | Danbury High School - Stadium Turf Field |
| THU 9/11 | 6:00 PM | Non-League | Daniel Hand | St. Joseph | Daniel Hand High School - Turf Field |
| THU 9/11 | Canceled | League | Hall | South Windsor | Hall High School - Football Practice Field |
| THU 9/11 | Canceled | League | New Milford | | New Milford High School - North Turf Field - NMHS |
| THU 9/11 | Canceled | Non-League | Danbury | Hamden | Danbury High School - Stadium Turf Field |
| FRI 9/12 | 3:45 PM | League | Farmington | Enfield | Farmington High School - Turf Field |
| SAT 9/13 | 10:00 AM | Non-League | Southington | Brien McMahon | Southington High School - 2 TURF FIELD |
| SAT 9/13 | 12:00 PM | Non-League | Ridgefield | New Fairfield | Ridgefield High School - Tiger Hollow Turf Field II |
| WED 9/17 | 3:45 PM | League | Manchester | Platt | Memorial Field @ MHS - Memorial Field @ MHS |
| WED 9/17 | 5:00 PM | Non-League | Masuk | Daniel Hand | Masuk High School - Benedict Stadium Field @ Masuk HS |
| WED 9/17 | 6:30 PM | League | Cheshire | Lyman Hall | Cheshire High School - Alumni Field - Turf |
| WED 9/17 | Canceled | League | Hamden | Lyman Hall | Hamden High School - HHS Turf #1 |
| WED 9/17 | Postponed | Non-League | Nonnewaug Chiefs | Pomperaug | Nonnewaug High School - football field |
| THU 9/18 | 3:45 PM | League | Bristol Central | Berlin | Bristol Central High School - BC Turf Field |
| THU 9/18 | 3:45 PM | League | Conard | Farmington | Conard High School - Football Field - Grass |
| THU 9/18 | 3:45 PM | League | East Hartford | Maloney | East Hartford High School - Freshman Practice Field |
| THU 9/18 | 3:45 PM | League | Simsbury | Newington | Holden Field - Turf |
| THU 9/18 | 3:45 PM | Non-League | Enfield | Rockville | Enfield High School - EHS TURF |
| THU 9/18 | 4:00 PM | League | Amity | Notre Dame-West Haven | Amity Regional High School - William Johnson Stadium Field |
| THU 9/18 | 4:00 PM | League | Newtown | New Milford | Newtown High School - Blue and Gold Stadium |
| THU 9/18 | 4:00 PM | League | St. Joseph | Danbury | St. Joseph High School - Upper Turf |
| THU 9/18 | 4:00 PM | League | Xavier | Fairfield Prep | Xavier High School - Larry McHugh Field |
| THU 9/18 | 4:30 PM | League | Shelton | West Haven | Shelton High School - Finn Stadium |
| THU 9/18 | 5:00 PM | League | Fairfield Ludlowe | Westhill | Fairfield Ludlowe High School - Taft Field |
| THU 9/18 | 5:30 PM | League | Darien | Brien McMahon | Darien High School - DHS Stadium East |
| THU 9/18 | 5:30 PM | League | New Canaan | Ridgefield | New Canaan HS - Dunning Stadium |
| THU 9/18 | 6:00 PM | League | Trumbull | Wilton | Trumbull High School - McDougall Stadium |
| THU 9/18 | 6:15 PM | League | Staples | Stamford | Staples High School - Staples Stadium |
| THU 9/18 | 6:30 PM | League | New Britain | Hall | Veteran's Stadium-Willow Brook Park - Football Field |
| THU 9/18 | Canceled | League | Bristol Eastern | Conard | Bristol Eastern High School - Alumni Field-Turf |
| THU 9/18 | Canceled | League | Cheshire | | Cheshire High School - Alumni Field - Turf |
| THU 9/18 | Canceled | League | Fairfield Warde | Bridgeport Central | Fairfield Warde High School - Tetreau/Davis Field |
| THU 9/18 | Canceled | League | North Haven | Daniel Hand | North Haven Middle School - Vanacore Field |
| FRI 9/19 | 5:00 PM | League | Greenwich | Norwalk | Greenwich High School - GHS Field 7 |
| FRI 9/19 | Canceled | League | Windsor | South Windsor | Windsor High School - Jack O'Brien Stadium |
| SAT 9/20 | 8:30 AM | League | Wethersfield | Avon | Wethersfield High School - Cottone Field |
| SAT 9/20 | 9:00 AM | League | Glastonbury | Southington | Glastonbury High School - Turf Field |
| WED 9/24 | 4:00 PM | League | Notre Dame-West Haven | Daniel Hand | Veterans Memorial Park (West Haven, CT) - Field |
| WED 9/24 | 4:00 PM | Non-League | Lyman Hall | Platt Tech | Lyman Hall High School - Fitzgerald Field |
| WED 9/24 | 6:30 PM | Non-League | Fairfield Ludlowe | Shelton | Fairfield Ludlowe High School - Taft Field |
| THU 9/25 | 3:30 PM | League | Berlin | Windsor | Sage Park Berlin - Scalise Field |
| THU 9/25 | 3:30 PM | Non-League | Harding | Joel Barlow | Warren Harding High School - Lewis Field |
| THU 9/25 | 3:45 PM | League | Bristol Central | North Haven | Bristol Central High School - BC Turf Field |
| THU 9/25 | 3:45 PM | League | Enfield | Newington | Enfield High School - EHS TURF |
| THU 9/25 | 3:45 PM | League | E.O. Smith | Farmington | Mansfield Middle School - Spring Hill Ball Field |
| THU 9/25 | 3:45 PM | Non-League | Southington | St. Joseph | Southington High School - 2 TURF FIELD |
| THU 9/25 | 4:00 PM | Non-League | Newtown | Ansonia | Newtown High School - Blue and Gold Stadium |
| THU 9/25 | 4:30 PM | Non-League | Masuk | Darien | Masuk High School - Benedict Stadium Field @ Masuk HS |
| THU 9/25 | 5:00 PM | Non-League | Nonnewaug Chiefs | Wilcox / Kaynor Football | Nonnewaug High School - football field |
| THU 9/25 | 5:00 PM | Non-League | Stamford | Guilford | Stamford High School - Boyle Stadium |
| THU 9/25 | 5:30 PM | League | Trumbull | Fairfield Warde | Trumbull High School - Cork Field |
| THU 9/25 | 5:30 PM | Non-League | Norwalk | New Milford | Nathan Hale Middle School - Callahan Complex at Nathan Hale Lower |
| THU 9/25 | 6:15 PM | League | Staples | West Haven | Staples High School - Staples Stadium |
| THU 9/25 | 6:30 PM | League | Ridgefield | Greenwich | Ridgefield High School - Tiger Hollow Turf Field II |
| THU 9/25 | Canceled | League | Hamden | | Hamden High School - HHS Turf #1 |
| THU 9/25 | Canceled | League | Berlin | Bristol Eastern | Sage Park Berlin - Scalise Field |
| THU 9/25 | Canceled | League | South Windsor | Avon | South Windsor High School - Field in front of HS |
| THU 9/25 | Canceled | Non-League | Danbury | Glastonbury | Danbury High School - Stadium Turf Field |
| SAT 9/27 | 10:00 AM | League | Stratford | Notre Dame Prep | Penders Field - Penders Field - Stratford |
| SAT 9/27 | 10:30 AM | League | East Hartford | Brien McMahon | East Hartford High School - Turf Field |
| SAT 9/27 | 12:00 PM | Non-League | New Britain | Fairfield Prep | Veteran's Stadium-Willow Brook Park - Football Field |
| SAT 9/27 | 8:30 AM | League | Wethersfield | Platt | Wethersfield High School - Cottone Field |
| SAT 9/27 | 9:30 AM | League | Maloney | Conard | Maloney High School - Turf Field |
| MON 9/29 | 5:00 PM | League | Simsbury | Hall | Holden Field - Turf |
| WED 10/1 | 3:30 PM | League | Cheshire | Notre Dame-West Haven | Cheshire High School - Alumni Field - Turf |
| WED 10/1 | 3:30 PM | League | Newtown | Stratford | Treadwell Park - Newtown Treadwell Park |
| WED 10/1 | 3:45 PM | League | Bristol Central | Windsor | Bristol Central High School - BC Turf Field |
| WED 10/1 | 3:45 PM | League | East Hartford | Conard | East Hartford High School - Freshman Practice Field |
| WED 10/1 | 3:45 PM | League | Enfield | New Britain | Enfield High School - EHS TURF |
| WED 10/1 | 3:45 PM | League | Platt | Glastonbury | Platt High School - Football Field |
| WED 10/1 | 3:45 PM | League | Berlin | Wethersfield | Sage Park Berlin - Scalise Field |
| WED 10/1 | 4:00 PM | League | Avon | Rockville | Avon High School - Turf Field |
| WED 10/1 | 4:00 PM | League | New Canaan | St. Joseph | New Canaan HS - WTT #1 |
| WED 10/1 | 4:00 PM | League | New Milford | Masuk | New Milford High School - North Turf Field - NMHS |
| WED 10/1 | 5:00 PM | League | Pomperaug | Bethel | Pomperaug High School - Stadium |
| WED 10/1 | Canceled | League | Amity | Sheehan | Amity Regional High School - William Johnson Stadium Field |
| WED 10/1 | Canceled | League | Cheshire | North Haven | Cheshire High School - Alumni Field - Turf |
| WED 10/1 | Canceled | League | Farmington | Bristol Eastern | Farmington High School - Turf Field |
| WED 10/1 | Canceled | League | Newington | Middletown | Newington High School - Abbate Field, Alumni Rd. |
| WED 10/1 | Canceled | League | Ansonia | Fairfield Prep | Nolan Field-Ansonia - Football Field |
| THU 10/2 | 4:00 PM | League | Xavier | West Haven | Xavier High School - Larry McHugh Field |
| THU 10/2 | 4:00 PM | Non-League | Lyman Hall | Wilcox / Kaynor Football | Lyman Hall High School - Fitzgerald Field |
| THU 10/2 | Canceled | League | Daniel Hand | Hamden | Daniel Hand High School - Turf Field |
| THU 10/2 | Canceled | League | South Windsor | Simsbury | South Windsor High School - Field in front of HS |
| FRI 10/3 | 3:00 PM | League | Maloney | Manchester | Falcon Field (Meriden, CT) - Turf |
| FRI 10/3 | 3:30 PM | League | Stamford | Brien McMahon | Stamford High School - Boyle Stadium |
| FRI 10/3 | 4:00 PM | League | Westhill | Greenwich | Rippowan MS - Rippowam Turf Field |
| FRI 10/3 | 4:15 PM | League | Wilton | Fairfield Ludlowe | Wilton High School - Fuijitani Field -Turf |
| FRI 10/3 | 5:30 PM | League | Norwalk | Ridgefield | Nathan Hale Middle School - Callahan Complex at Nathan Hale Lower |
| FRI 10/3 | 6:00 PM | League | Staples | Darien | Staples High School - Staples Stadium |
| SAT 10/4 | 10:00 AM | League | Danbury | Fairfield Warde | Danbury High School - Stadium Turf Field |
| SAT 10/4 | 10:00 AM | League | Joel Barlow | Brookfield | Joel Barlow High School - Field I (Stadium) |
| SAT 10/4 | 8:30 AM | League | Hall | Southington | Hall High School - Football Practice Field |
| SAT 10/4 | 9:00 AM | League | Fairfield Prep | Shelton | Fairfield University - Barlow Field |
| THU 10/9 | 3:45 PM | League | Bristol Central | Hall | Bristol Central High School - BC Turf Field |
| THU 10/9 | 3:45 PM | League | Conard | Farmington | Conard High School - Football Field - Grass |
| THU 10/9 | 3:45 PM | League | Enfield | Windsor | Enfield High School - EHS TURF |
| THU 10/9 | 3:45 PM | League | Simsbury | East Hartford | Holden Field - Turf |
| THU 10/9 | 3:45 PM | League | Manchester | Glastonbury | Memorial Field @ MHS - Memorial Field @ MHS |
| THU 10/9 | 3:45 PM | League | New Britain | Southington | Veteran's Stadium-Willow Brook Park - Football Field |
| THU 10/9 | 3:45 PM | Non-League | Newington | Xavier | Newington High School - Abbate Field, Alumni Rd. |
| THU 10/9 | 4:00 PM | League | Cheshire | Daniel Hand | Cheshire High School - Alumni Field - Turf |
| THU 10/9 | 4:00 PM | League | Danbury | New Canaan | Danbury High School - Stadium Turf Field |
| THU 10/9 | 4:00 PM | League | Fairfield Ludlowe | Norwalk | Fairfield Ludlowe High School - Taft Field |
| THU 10/9 | 4:00 PM | League | Fairfield Prep | West Haven | Fairfield University - Rafferty Stadium |
| THU 10/9 | 4:00 PM | League | Shelton | Lyman Hall | Shelton High School - Finn Stadium |
| THU 10/9 | 4:00 PM | League | Notre Dame-West Haven | North Haven | Veterans Memorial Park (West Haven, CT) - Field |
| THU 10/9 | 4:30 PM | League | Harding | Amity | Warren Harding High School - Lewis Field |
| THU 10/9 | 5:00 PM | League | Greenwich | Trumbull | Greenwich High School - GHS Field 7 |
| THU 10/9 | 5:00 PM | League | Stamford | Fairfield Warde | Stamford High School - Boyle Stadium |
| THU 10/9 | 6:00 PM | League | Ridgefield | St. Joseph | Ridgefield High School - Tiger Hollow Stadium |
| THU 10/9 | 6:15 PM | League | Staples | Wilton | Staples High School - Staples Stadium |
| THU 10/9 | Canceled | League | Conard | South Windsor | Conard High School - Football Field - Grass |
| THU 10/9 | Canceled | League | Hamden | Hillhouse | Hamden High School - HHS Turf #1 |
| SAT 10/11 | 10:00 AM | League | Brien McMahon | Westhill | Brien McMahon High School - Casagrande Field |
| SAT 10/11 | 9:30 AM | League | Naugatuck | Watertown | Naugatuck High School - Veterans Field |
| WED 10/15 | 5:00 PM | League | Stratford | New Fairfield | Penders Field - Penders Field - Stratford |
| THU 10/16 | 3:45 PM | League | Avon | Berlin | Avon High School - Turf Field |
| THU 10/16 | 3:45 PM | Non-League | Platt | Masuk | Platt High School - Platt Turf field |
| THU 10/16 | 4:00 PM | Non-League | Amity | Trumbull | Amity Regional High School - William Johnson Stadium Field |
| THU 10/16 | 4:00 PM | Non-League | Maloney | Fairfield Prep | Maloney High School - Turf Field |
| THU 10/16 | 5:00 PM | League | Cheshire | Shelton | Cheshire High School - Alumni Field - Turf |
| THU 10/16 | 5:30 PM | League | Joel Barlow | Pomperaug | Joel Barlow High School - Field I (Stadium) |
| THU 10/16 | Canceled | League | Bristol Eastern | Middletown | Bristol Eastern High School - Alumni Field-Turf |
| THU 10/16 | Canceled | Non-League | Platt | | Platt High School - Platt Turf field |
| FRI 10/17 | 4:30 PM | Non-League | Bridgeport Central | Harding | Bridgeport Central High School - Kennedy Stadium |
| FRI 10/17 | 6:30 PM | League | Daniel Hand | Xavier | Daniel Hand High School - Turf Field |
| SAT 10/18 | 10:30 AM | League | Nonnewaug Chiefs | Platt Tech | Nonnewaug High School - football field |
| SAT 10/18 | 10:30 AM | Non-League | Nonnewaug Chiefs | Platt Tech | Nonnewaug High School - football field |
| SAT 10/18 | Canceled | League | Wethersfield | E.O. Smith | Wethersfield High School - Cottone Field |
| TUE 10/21 | 6:30 PM | Non-League | Avon | Wilcox / Kaynor Football | Avon High School - Turf Field |
| WED 10/22 | 3:30 PM | League | Notre Dame-West Haven | Amity | Veterans Memorial Park (West Haven, CT) - Field |
| WED 10/22 | 3:45 PM | League | Enfield | East Hartford | Enfield High School - EHS TURF |
| WED 10/22 | 3:45 PM | League | New Britain | Glastonbury | Veteran's Stadium-Willow Brook Park - Football Field |
| WED 10/22 | 4:30 PM | League | New Fairfield | Joel Barlow | New Fairfield High School - Stadium Field |
| WED 10/22 | 6:00 PM | League | Fairfield Warde | Staples | Fairfield Warde High School - Tetreau/Davis Field |
| WED 10/22 | Canceled | League | South Windsor | Bristol Central | South Windsor High School - Field in front of HS |
| THU 10/23 | 3:30 PM | League | Westhill | Norwalk | Westhill High School - J. Walter Kennedy Stadium |
| THU 10/23 | 3:30 PM | League | Windsor | Conard | Windsor High School - Jack O'Brien Stadium |
| THU 10/23 | 3:30 PM | Non-League | Masuk | Fairfield Prep | Masuk High School - Benedict Stadium Field @ Masuk HS |
| THU 10/23 | 3:45 PM | League | Hall | Maloney | Hall High School - Football Practice Field |
| THU 10/23 | 3:45 PM | League | Manchester | Southington | Memorial Field @ MHS - Memorial Field @ MHS |
| THU 10/23 | 3:45 PM | League | Newington | Berlin | Newington High School - Abbate Field, Alumni Rd. |
| THU 10/23 | 3:45 PM | League | Platt | Simsbury | Platt High School - Football Field |
| THU 10/23 | 4:00 PM | League | Lyman Hall | Harding | Lyman Hall High School - Fitzgerald Field |
| THU 10/23 | 4:00 PM | League | Shelton | Daniel Hand | Shelton High School - Finn Stadium |
| THU 10/23 | 4:00 PM | League | St. Joseph | Darien | St. Joseph High School - Upper Turf |
| THU 10/23 | 4:00 PM | League | West Haven | Cheshire | West Haven High School - Ken Strong Stadium |
| THU 10/23 | 5:00 PM | League | Brien McMahon | Danbury | Brien McMahon High School - Casagrande Field |
| THU 10/23 | 5:00 PM | League | New Canaan | Greenwich | New Canaan HS - Dunning Stadium |
| THU 10/23 | 5:00 PM | League | Stamford | Wilton | Stamford High School - Boyle Stadium |
| THU 10/23 | 6:00 PM | League | Trumbull | Fairfield Ludlowe | Trumbull High School - McDougall Stadium |
| THU 10/23 | 7:00 PM | Non-League | Ridgefield | Pomperaug | Ridgefield High School - Tiger Hollow Stadium |
| THU 10/23 | Canceled | League | Hillhouse | Amity | Bowen Field - Football Field |
| THU 10/23 | Canceled | League | Bristol Eastern | Wethersfield | Bristol Eastern High School - Alumni Field-Turf |
| THU 10/23 | Canceled | League | Farmington | Northwest Catholic | Farmington High School - Turf Field |
| THU 10/23 | Canceled | League | Hamden | | Hamden High School - HHS Turf #1 |
| THU 10/23 | Canceled | League | North Haven | Sheehan | North Haven Middle School - Vanacore Field |
| FRI 10/24 | Canceled | League | Middletown | E.O. Smith | Middletown High School - MHS Stadium |
| SAT 10/25 | 10:00 AM | League | Crosby | Holy Cross | Crosby High School - CHS - Jimmy Lee Stadium (Turf) |
| SAT 10/25 | 10:00 AM | League | Northwest Catholic | Farmington | Northwest Catholic High School (Primary) - Neil J. Brewer Field |
| WED 10/29 | 3:30 PM | League | Conard | Manchester | Conard High School - Football Field - Grass |
| WED 10/29 | 3:45 PM | League | Maloney | New Britain | Falcon Field (Meriden, CT) - Turf |
| WED 10/29 | 3:45 PM | League | Farmington | Wethersfield | Farmington High School - Turf Field |
| WED 10/29 | 3:45 PM | League | Berlin | Enfield | Sage Park Berlin - Scalise Field |
| WED 10/29 | 4:00 PM | League | Masuk | Stratford | Masuk High School - Benedict Stadium Field @ Masuk HS |
| WED 10/29 | 4:00 PM | League | Notre Dame-West Haven | | Veterans Memorial Park (West Haven, CT) - Field |
| WED 10/29 | 4:00 PM | League | Xavier | Lyman Hall | Xavier High School - Larry McHugh Field |
| WED 10/29 | 5:00 PM | Non-League | Cheshire | Norwalk | Cheshire High School - Alumni Field - Turf |
| WED 10/29 | Canceled | League | Hillhouse | Cheshire | Bowen Field - Football Field |
| WED 10/29 | Canceled | League | Danbury | Norwalk | Danbury High School - Stadium Turf Field |
| THU 10/30 | 3:45 PM | League | Glastonbury | Hall | Glastonbury High School - Turf Field |
| THU 10/30 | 3:45 PM | League | Northwest Catholic | Avon | Northwest Catholic High School (Primary) - Neil J. Brewer Field |
| THU 10/30 | 4:00 PM | League | Amity | West Haven | Amity Regional High School - William Johnson Stadium Field |
| THU 10/30 | 4:00 PM | League | Darien | Trumbull | Darien High School - DHS Stadium East |
| THU 10/30 | 4:00 PM | League | Fairfield Prep | North Haven | Fairfield University - Rafferty Stadium |
| THU 10/30 | 4:00 PM | League | Staples | St. Joseph | Staples High School - Staples Stadium |
| THU 10/30 | 5:00 PM | League | Fairfield Ludlowe | Greenwich | Fairfield Ludlowe High School - Taft Field |
| THU 10/30 | Canceled | League | Newtown | Pomperaug | Newtown High School - Blue and Gold Stadium |
| THU 10/30 | Postponed | League | Fairfield Warde | Wilton | Fairfield Warde High School - Tetreau/Davis Field |
| FRI 10/31 | 3:45 PM | League | Bristol Central | East Hartford | Bristol Central High School - BC Turf Field |
| FRI 10/31 | 3:45 PM | League | New Canaan | Stamford | New Canaan HS - Dunning Stadium |
| FRI 10/31 | 3:45 PM | League | Southington | Platt | Southington High School - 2 TURF FIELD |
| FRI 10/31 | Canceled | League | E.O. Smith | Newington | Mansfield Middle School - Spring Hill Ball Field |
| SAT 11/1 | 10:00 AM | League | Pomperaug | New Fairfield | Pomperaug High School - Stadium |
| SAT 11/1 | 10:00 AM | League | Ridgefield | Brien McMahon | Ridgefield High School - Tiger Hollow Turf Field II |
| SAT 11/1 | 9:00 AM | League | Windsor | Simsbury | Windsor High School - Jack O'Brien Stadium |
| WED 11/5 | 6:30 PM | League | Pomperaug | Bunnell | Pomperaug High School - Stadium |
| THU 11/6 | 3:15 PM | League | Hall | Manchester | Hall High School - Stadium (Turf Field) |
| THU 11/6 | 3:15 PM | League | St. Joseph | Fairfield Ludlowe | St. Joseph High School - Lower Turf |
| THU 11/6 | 3:45 PM | League | Enfield | Bristol Central | Enfield High School - EHS TURF |
| THU 11/6 | 3:45 PM | League | Maloney | Glastonbury | Falcon Field (Meriden, CT) - Turf |
| THU 11/6 | 3:45 PM | League | New Britain | Farmington | Veteran's Stadium-Willow Brook Park - Football Field |
| THU 11/6 | 3:45 PM | Non-League | Platt | E.O. Smith | Platt High School - Platt Turf field |
| THU 11/6 | 3:45 PM | Non-League | Berlin | Stratford | Sage Park Berlin - Scalise Field |
| THU 11/6 | 4:00 PM | League | Lyman Hall | Amity | Lyman Hall High School - Fitzgerald Field |
| THU 11/6 | 4:15 PM | League | Conard | Simsbury | Conard High School - Football Field - Grass |
| THU 11/6 | 4:15 PM | League | Wilton | Greenwich | Wilton High School - Fuijitani Field -Turf |
| THU 11/6 | 4:30 PM | League | Daniel Hand | Fairfield Prep | Madison Surf Club - Strong Field |
| THU 11/6 | 5:00 PM | League | Brien McMahon | Trumbull | Brien McMahon High School - Casagrande Field |
| THU 11/6 | 5:00 PM | Non-League | Danbury | ATI | Danbury High School - Stadium Turf Field |
| THU 11/6 | 5:30 PM | League | Darien | Ridgefield | Darien High School - DHS Stadium Field |
| THU 11/6 | 5:30 PM | League | Joel Barlow | Masuk | Joel Barlow High School - Field I (Stadium) |
| THU 11/6 | 5:30 PM | League | Norwalk | Stamford | Nathan Hale Middle School - Callahan Complex at Nathan Hale Lower |
| THU 11/6 | 6:00 PM | League | Shelton | Notre Dame-West Haven | Shelton High School - Finn Stadium |
| THU 11/6 | 6:00 PM | League | Southington | Windsor | Southington High School - 2 TURF FIELD |
| THU 11/6 | 6:15 PM | League | Staples | New Canaan | Staples High School - Staples Stadium |
| THU 11/6 | Canceled | League | East Hartford | South Windsor | East Hartford High School - Freshman Practice Field |
| THU 11/6 | Canceled | League | Hamden | | Hamden High School - HHS Turf #1 |
| THU 11/6 | Canceled | League | Lyman Hall | East Haven | Lyman Hall High School - Fitzgerald Field |
| THU 11/6 | Canceled | League | E.O. Smith | Bristol Eastern | Mansfield Middle School - Spring Hill Ball Field |
| THU 11/6 | Canceled | League | Northwest Catholic | Newington | Northwest Catholic High School (Primary) - Neil J. Brewer Field |
| THU 11/6 | Canceled | League | Sheehan | Cheshire | Sheehan High School - Sheehan HS Riccitelli Field (Turf) |
| THU 11/6 | Canceled | League | Harding | Foran | Warren Harding High School - Lewis Field |
| THU 11/6 | Postponed | League | Xavier | West Haven | Xavier High School - Larry McHugh Field |
| FRI 11/7 | 3:45 PM | League | Avon | Plainville | Avon High School - Turf Field |
| SAT 11/8 | 10:00 AM | League | Fairfield Warde | Westhill | Fairfield Warde High School - Tetreau/Davis Field |
| WED 11/12 | 3:30 PM | League | Wethersfield | Northwest Catholic | Wethersfield High School - Cottone Field |
| WED 11/12 | 3:45 PM | Non-League | Berlin | Lyman Hall | Sage Park Berlin - Scalise Field |
| WED 11/12 | 5:00 PM | League | Stratford | New Milford | Penders Field - Penders Field - Stratford |
| THU 11/13 | 2:45 PM | League | Westhill | Danbury | Westhill High School - J. Walter Kennedy Stadium |
| THU 11/13 | 3:15 PM | League | Southington | Maloney | Southington High School - 2 TURF FIELD |
| THU 11/13 | 3:45 PM | League | East Hartford | Windsor | East Hartford High School - Freshman Practice Field |
| THU 11/13 | 3:45 PM | League | Simsbury | Bristol Central | Holden Field - Turf |
| THU 11/13 | 3:45 PM | League | Manchester | New Britain | Memorial Field @ MHS - Memorial Field @ MHS |
| THU 11/13 | 3:45 PM | League | Platt | Hall | Platt High School - Football Field |
| THU 11/13 | 3:45 PM | Non-League | Glastonbury | Fairfield Prep | Glastonbury High School - Turf Field |
| THU 11/13 | 4:00 PM | League | Amity | Cheshire | Amity Regional High School - William Johnson Stadium Field |
| THU 11/13 | 4:00 PM | League | Pomperaug | Masuk | Pomperaug High School - Stadium |
| THU 11/13 | 4:00 PM | Non-League | Rockville | Enfield | Rockville High School - Stadium Field |
| THU 11/13 | 4:00 PM | Non-League | Notre Dame-West Haven | Ansonia | Veterans Memorial Park (West Haven, CT) - Field |
| THU 11/13 | 4:15 PM | League | Wilton | St. Joseph | Wilton High School - Fuijitani Field -Turf |
| THU 11/13 | 4:30 PM | League | Farmington | Conard | Farmington High School - Turf Field |
| THU 11/13 | 4:30 PM | League | West Haven | Daniel Hand | West Haven High School - Ken Strong Stadium |
| THU 11/13 | 5:00 PM | League | Darien | Greenwich | Darien High School - DHS Stadium Field |
| THU 11/13 | 5:00 PM | League | Fairfield Ludlowe | Staples | Fairfield Ludlowe High School - Taft Field |
| THU 11/13 | 5:30 PM | League | Norwalk | Fairfield Warde | Nathan Hale Middle School - Callahan Complex at Nathan Hale Lower |
| THU 11/13 | 6:00 PM | League | Ridgefield | Stamford | Ridgefield High School - Tiger Hollow Stadium |
| THU 11/13 | 6:00 PM | League | Trumbull | New Canaan | Trumbull High School - McDougall Stadium |
| THU 11/13 | 6:00 PM | Non-League | Newtown | Shelton | Newtown High School - Blue and Gold Stadium |
| THU 11/13 | 7:00 PM | League | Xavier | Harding | Xavier High School - Larry McHugh Field |
| THU 11/13 | Canceled | League | Farmington | Conard | Farmington High School - Turf Field |
| THU 11/13 | Canceled | League | Glastonbury | South Windsor | Glastonbury High School - Turf Field |
| THU 11/13 | Canceled | League | Lyman Hall | Guilford | Lyman Hall High School - Fitzgerald Field |
| THU 11/13 | Canceled | League | North Haven | Hamden | North Haven Middle School - Vanacore Field |
| THU 11/13 | Canceled | League | Notre Dame-West Haven | Hillhouse | Veterans Memorial Park (West Haven, CT) - Field |
| FRI 11/14 | Canceled | League | Bristol Eastern | Newington | Bristol Eastern High School - Alumni Field-Turf |
| FRI 11/14 | Canceled | League | E.O. Smith | Berlin | Mansfield Middle School - Spring Hill Ball Field |
| MON 11/17 | 5:45 PM | League | Bristol Central | E.O. Smith | Bristol Central High School - BC Turf Field |
| TUE 11/18 | 3:30 PM | League | Maloney | Platt | Falcon Field (Meriden, CT) |
| TUE 11/18 | 5:00 PM | League | New Canaan | Darien | New Canaan HS - Dunning Stadium |
| WED 11/19 | 6:00 PM | League | Daniel Hand | Lyman Hall | Madison Surf Club - Strong Field |
| WED 11/19 | 6:30 PM | League | Bullard Havens Tech | Platt Tech | Kennedy Stadium (Bridgeport) - Kennedy Stadium (Bridgeport) |
| THU 11/20 | 3:30 PM | League | Greenwich | Staples | Greenwich High School - Cardinal Stadium |
| THU 11/20 | 3:45 PM | League | Avon | Farmington | Avon High School - Turf Field |
| THU 11/20 | 3:45 PM | League | Newington | Wethersfield | Clem Lemire Complex - Turf Field |
| THU 11/20 | 3:45 PM | League | East Hartford | Manchester | East Hartford High School - Freshman Practice Field |
| THU 11/20 | 3:45 PM | League | Glastonbury | Simsbury | Glastonbury High School - Turf Field |
| THU 11/20 | 3:45 PM | League | Berlin | New Britain | Sage Park Berlin - Scalise Field |
| THU 11/20 | 4:00 PM | League | Hall | Conard | Hall High School - Stadium (Turf Field) |
| THU 11/20 | 4:00 PM | League | Masuk | Newtown | Masuk High School - Benedict Stadium Field @ Masuk HS |
| THU 11/20 | 4:00 PM | League | New Milford | New Fairfield | New Milford High School - North Turf Field - NMHS |
| THU 11/20 | 4:00 PM | League | North Haven | West Haven | North Haven Middle School - Vanacore Field |
| THU 11/20 | 4:00 PM | League | Stamford | Westhill | Stamford High School - Boyle Stadium |
| THU 11/20 | 4:00 PM | League | Notre Dame-West Haven | Hamden | Veterans Memorial Park (West Haven, CT) - Field |
| THU 11/20 | 5:00 PM | League | Amity | Shelton | Amity Regional High School - William Johnson Stadium Field |
| THU 11/20 | 5:00 PM | League | Ridgefield | Wilton | Ridgefield High School - Tiger Hollow Stadium |
| THU 11/20 | 5:00 PM | Non-League | Cheshire | Southington | Cheshire High School - Alumni Field - Turf |
| THU 11/20 | 5:30 PM | League | Norwalk | Brien McMahon | Nathan Hale Middle School - Callahan Complex at Nathan Hale Lower |
| THU 11/20 | 6:00 PM | League | Fairfield Warde | Fairfield Ludlowe | Fairfield Warde High School - Tetreau/Davis Field |
| THU 11/20 | 6:00 PM | League | Stratford | Bunnell | Penders Field - Penders Field - Stratford |
| THU 11/20 | 6:00 PM | League | Trumbull | St. Joseph | Trumbull High School - McDougall Stadium |
| THU 11/20 | Canceled | League | Bristol Central | Bristol Eastern | Bristol Central High School - BC Turf Field |
| THU 11/20 | Canceled | League | Danbury | Ridgefield | Danbury High School - Stadium Turf Field |
| THU 11/20 | Canceled | League | Northwest Catholic | E.O. Smith | Northwest Catholic High School (Primary) - NWC Lacrosse Field |
| THU 11/20 | Canceled | League | Sheehan | Lyman Hall | Sheehan High School - Sheehan HS Riccitelli Field (Turf) |
| THU 11/20 | Canceled | League | South Windsor | Enfield | South Windsor High School - Field in front of HS |
| THU 11/20 | Canceled | Non-League | Hillhouse | Wilton | Bowen Field - Football Field |
| FRI 11/21 | 3:45 PM | Non-League | VG Titans | Wilcox / Kaynor Football | Pat Kidney Sports Complex - Football Field |
| FRI 11/21 | 4:00 PM | League | Stratford | Bunnell | Penders Field - Penders Field - Stratford |
| FRI 11/21 | 4:30 PM | Non-League | Enfield | Coventry/Windham Tech/Bolton Football | Enfield High School - EHS TURF |
| MON 11/24 | Canceled | League | Hillhouse | Wilbur Cross | Bowen Field - Football Field |