| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 12/13 | 6:00 PM | Varsity | League | Normal | Away | Bethel | | | | Bethel High School - BHS gym | 4:30 PM - 1 Bus |
| SAT 12/16 | 9:00 AM | Varsity | League | Normal | Away | St. Joseph | | | | Fairfield Ludlowe High School - Main Gym | 7:00 AM - 1 Bus |
| Enfield | | |
| Stamford | | |
| Branford | | |
| Fairfield Prep | | |
| Brien McMahon | | |
| Westhill | | |
| Bethel | | |
| Stratford | | |
| Pomperaug | | |
| Norwalk | | |
| Fairfield Ludlowe | | |
| THU 12/21 | 6:00 PM | Varsity | League | Normal | Away | Notre Dame-Fairfield | | | | Notre Dame - Fairfield - Sister Marion Reilly Auditorium | 4:15 PM - 1 Bus |
| FRI 12/22 | 3:00 PM | Varsity | League | Normal | Away | New Milford | | | | New Milford High School - Small Gym - NMHS | 1:30 PM - 1 Bus |
| Shelton | | |
| East Hartford | | |
| WED 12/27 | 9:00 AM | Varsity | Tournament | Normal | Away | Fairfield Prep | | | | Newtown High School - Gym | 6:45 AM - 1 Bus |
| Branford | | |
| Montville | | |
| Newtown | | |
| Notre Dame-West Haven | | |
| Norwalk | | |
| Stratford | | |
| WED 1/3 | 6:00 PM | Varsity | League | Normal | Home | New Milford | | | | Joel Barlow High - Upper Gym | |
| SAT 1/6 | 9:00 AM | Varsity | Non-League | Normal | Away | Derby/Oxford/Holy Cross | | | | Canton High School - Gym | 6:00 AM - 1 Bus |
| Haddam Killingworth | | |
| Somers | | |
| Cheshire | | |
| Northwestern | | |
| Old Lyme | | |
| St. Paul Catholic | | |
| Bacon Academy | | |
| Canton | | |
| Windsor | | |
| Nonnewaug | | |
| Morgan | | |
| THU 1/11 | 6:00 PM | Varsity | League | Normal | Away | Pomperaug | | | | Pomperaug High School - Auxiliary Gym | 4:00 PM - 1 Bus |
| SAT 1/13 | 9:00 AM | Varsity | Non-League | Normal | Away | Cheshire | | | | Fairfield Ludlowe High School - Main Gym | 7:15 AM - 1 Bus |
| New Haven Wrestling | | |
| Fairfield Ludlowe | | |
| Fairfield Warde | | |
| WED 1/17 | 6:00 PM | Varsity | League | Normal | Home | Brookfield/Shepaug | | | | Joel Barlow High - Upper Gym | |
| SAT 1/20 | 9:00 AM | Varsity | League | Normal | Away | Enfield | | | | New Milford High School - Main Gym - NMHS | 6:45 AM - 1 Bus |
| New Milford | | |
| Pomperaug | | |
| Amity | | |
| Stratford | | |
| Weston | | |
| Masuk | | |
| Maloney | | |
| Bunnell | | |
| Terryville-Thomaston | | |
| Norwalk | | |
| RHAM | | |
| Bethel | | |
| Bridgeport High Schools | | |
| WED 1/24 | 6:00 PM | Varsity | League | Normal | Home | New Fairfield | | | | Joel Barlow High - Upper Gym | |
| SAT 1/27 | 9:30 AM | Varsity | Tournament | Normal | Away | Wilton | | | | Brookfield High School - BHS Small & Big Gym | 6:45 AM - 1 Bus |
| Masuk | | |
| Danbury | | |
| Derby/Oxford/Holy Cross | | |
| Darien | | |
| Shelton | | |
| Brookfield/Shepaug | | |
| Pomperaug | | |
| Jonathan Law | | |
| New Canaan | | |
| St. Joseph | | |
| Stamford | | |
| Westhill | | |
| WED 1/31 | 6:00 PM | Varsity | League | Normal | Home | Weston | | | | Joel Barlow High - Upper Gym | |
| TUE 2/6 | 6:00 PM | Varsity | League | Normal | Away | Masuk | | | | Masuk High School - David Strong Gymnasium @ Masuk HS | 4:00 PM - 1 Bus |