| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 12/13 | 7:00 PM | Varsity | League | Normal | Away | Staples | | | | Staples High School - Field House | 5:45 PM |
| SAT 12/16 | 9:00 AM | Varsity | League | Normal | Away | Bethel | | | | Fairfield Ludlowe High School - Main Gym | 7:30 AM |
| Stratford | | |
| Brien McMahon | | |
| Fairfield Prep | | |
| Branford | | |
| Fairfield Ludlowe | | |
| Pomperaug | | |
| Enfield | | |
| St. Joseph | | |
| Joel Barlow | | |
| Stamford | | |
| Westhill | | |
| TUE 12/19 | 7:00 PM | Varsity | League | Normal | Home | Ridgefield | | | | Norwalk High School - Tom Scarso Gymnasium | |
| WED 12/27 | 9:00 AM | Varsity | Tournament | Normal | Away | Stratford | | | | Newtown High School - Gym | 6:45 AM |
| Branford | | |
| Fairfield Prep | | |
| Newtown | | |
| Montville | | |
| Notre Dame-West Haven | | |
| Joel Barlow | | |
| SAT 12/30 | 10:00 AM | Varsity | League | Normal | Away | Darien | | | | Fairfield Warde High School - Small Gym | 8:30 AM |
| Fairfield Warde | | |
| Brien McMahon | | |
| TUE 1/2 | 7:00 PM | Varsity | League | Normal | Home | Greenwich | | | | Norwalk High School - Tom Scarso Gymnasium | |
| WED 1/10 | Postponed | Varsity | League | Postponed | Away | Danbury | | | | Danbury High School - New gym | 3:00 PM |
| THU 1/18 | 6:00 PM | Varsity | League | Normal | Away | Stamford | | | | Stamford High School - Kuczo Gymnasium | 4:30 PM |
| SAT 1/20 | 9:00 AM | Varsity | League | Normal | Away | Bridgeport High Schools | | | | New Milford High School - Main Gym - NMHS | 6:30 AM |
| Bethel | | |
| Weston | | |
| RHAM | | |
| Joel Barlow | | |
| Pomperaug | | |
| Terryville-Thomaston | | |
| Masuk | | |
| Amity | | |
| New Milford | | |
| Maloney | | |
| Bunnell | | |
| Stratford | | |
| Enfield | | |
| WED 1/24 | 7:00 PM | Varsity | League | Normal | Home | Trumbull | | | | Norwalk High School - Tom Scarso Gymnasium | |
| SAT 1/27 | 9:00 AM | Varsity | Non-League | Normal | Away | Fairfield Prep | | | | Ridgefield High School - Main Gym | |
| Newtown | | |
| Amity | | |
| Bethel | | |
| Bunnell | | |
| New Milford | | |
| Bristol Central | | |
| Greenwich | | |
| Ridgefield | | |
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| WED 1/31 | 5:00 PM | Varsity | League | Normal | Away | Danbury | | | | Danbury High School - New gym | |
| Brien McMahon | | |
| TUE 2/6 | 6:00 PM | Varsity | League | Normal | Away | Westhill | | | | Westhill High School - New Gym | 4:30 PM |
| FRI 2/9 | 4:30 PM | Varsity | Tournament | Normal | Away | Wilton | | | | New Canaan HS - Main Gym | |
| Trumbull | | |
| Staples | | |
| Greenwich | | |
| Fairfield Warde | | |
| Danbury | | |
| Fairfield Ludlowe | | |
| Westhill | | |
| New Canaan | | |
| Darien | | |
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| Stamford | | |
| St. Joseph | | |
| Brien McMahon | | |
| Ridgefield | | |