| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 12/9 | 8:00 AM | Varsity | Scrimmage | Normal | Away | Shelton | | | | Staples High School - Field House | 7:30 AM |
| Staples | | |
| WED 12/13 | 6:00 PM | Varsity | League | Normal | Away | Brookfield/Shepaug | | | | Brookfield High School - BHS Big Gym | 4:00 PM - 1 Bus |
| WED 12/20 | 6:30 PM | Varsity | League | Normal | Home | Newtown | | | | Bunnell HS - David Johnson Gymnasium | |
| FRI 12/29 | 9:00 AM | Varsity | League | Normal | Away | Derby/Oxford/Holy Cross | | | | Jonathan Law High School - James L. Richetelli Memorial Gymnasium | 7:30 AM - 1 Bus |
| Jonathan Law | | |
| North Haven | | |
| Platt | | |
| Terryville-Thomaston | | |
| New Haven Wrestling | | |
| SAT 12/30 | 9:00 AM | Varsity | Non-League | Normal | Away | Bristol Eastern | | | | Morgan School - Gym | 7:00 AM - 1 Bus |
| Daniel Hand | | |
| East Haven | | |
| Farmington | | |
| Haddam Killingworth | | |
| Old Lyme | | |
| Morgan | | |
| Portland/Cromwell | | |
| Shelton | | |
| WED 1/3 | 6:00 PM | Varsity | League | Normal | Away | New Fairfield | | | | New Fairfield High School - Old High School Gym | 4:00 PM - 1 Bus |
| TUE 1/9 | 6:00 PM | Varsity | League | Normal | Home | Masuk | | | | Bunnell HS - David Johnson Gymnasium | |
| SAT 1/13 | 9:00 AM | Varsity | Tournament | Normal | Home | Amity | | | | Bunnell HS - David Johnson Gymnasium | |
| Canton | | |
| Notre Dame-Fairfield | | |
| Wilton | | |
| THU 1/18 | 6:00 PM | Varsity | League | Normal | Home | Bethel | | | | Bunnell HS - David Johnson Gymnasium | |
| SAT 1/20 | 9:00 AM | Varsity | League | Normal | Away | Amity | | | | New Milford High School - Main Gym - NMHS | 7:00 AM - 1 Bus |
| Bethel | | |
| Enfield | | |
| Joel Barlow | | |
| Maloney | | |
| Masuk | | |
| New Milford | | |
| Norwalk | | |
| Pomperaug | | |
| RHAM | | |
| Stratford | | |
| Terryville-Thomaston | | |
| Bridgeport High Schools | | |
| Weston | | |
| WED 1/24 | 6:00 PM | Varsity | League | Normal | Away | New Milford | | | | New Milford High School - Small Gym - NMHS | 4:00 PM - 1 Bus |
| SAT 1/27 | 9:00 AM | Varsity | Non-League | Normal | Away | | | | | Ridgefield High School - Main Gym | 7:30 AM - 1 Bus |
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| Amity | | |
| Bethel | | |
| Bristol Central | | |
| Fairfield Prep | | |
| Greenwich | | |
| New Milford | | |
| Newtown | | |
| Norwalk | | |
| Ridgefield | | |
| WED 1/31 | 6:00 PM | Varsity | League | Normal | Away | Stratford | | | | Stratford High School - Gym | 4:00 PM - 1 Bus |
| SAT 2/3 | 9:00 AM | Varsity | Non-League | Normal | Away | Amity | | | | Foran High School - Edna L. Fraser Gymnasium | 7:30 AM - 1 Bus |
| Darien | | |
| Jonathan Law | | |
| Foran | | |
| Stratford | | |
| TUE 2/6 | 6:00 PM | Varsity | League | Normal | Home | Notre Dame-Fairfield | | | | Bunnell HS - David Johnson Gymnasium | |