| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 12/13 | 6:00 PM | Varsity | League | Normal | Home | Masuk | | | | Weston High School - Gym (New) | |
| WED 12/20 | 6:00 PM | Varsity | League | Normal | Home | Brookfield/Shepaug | | | | Weston High School - Gym (New) | |
| WED 1/3 | 7:00 PM | Varsity | League | Normal | Away | Newtown | | | | Newtown High School - Gym | 5:00 PM |
| WED 1/10 | 6:00 PM | Varsity | League | Normal | Home | Notre Dame-Fairfield | | | | Weston High School - Gym (New) | |
| FRI 1/12 | 6:00 PM | Varsity | League | Normal | Home | Darien | | | | Weston High School - Gym (New) | |
| WED 1/17 | 6:00 PM | Varsity | League | Normal | Away | New Fairfield | | | | New Fairfield High School - Old High School Gym | 4:00 PM |
| SAT 1/20 | 9:00 AM | Varsity | League | Normal | Away | Amity | | | | New Milford High School - Main Gym - NMHS | 7:00 AM |
| Bethel | | |
| Bunnell | | |
| Enfield | | |
| Joel Barlow | | |
| Maloney | | |
| Masuk | | |
| New Milford | | |
| Norwalk | | |
| Pomperaug | | |
| RHAM | | |
| Stratford | | |
| Terryville-Thomaston | | |
| Bridgeport High Schools | | |
| SAT 1/20 | 9:30 AM | Other | Tournament | Normal | Away | Danbury | | | | Danbury High School - Main Gym | |
| Enfield | | |
| Fairfield Ludlowe | | |
| Fairfield Warde | | |
| New Canaan | | |
| New Fairfield | | |
| Newtown | | |
| Norwalk | | |
| Ridgefield | | |
| Simsbury | | |
| Southington | | |
| Stamford | | |
| Trumbull | | |
| WED 1/24 | 6:00 PM | Varsity | League | Normal | Home | Pomperaug | Win | 54-24 | | Weston High School - Gym (Old) | |
| SAT 1/27 | 8:00 AM | Other | Non-League | Normal | Away | Brien McMahon | | | | Norwalk High School - Tom Scarso Gymnasium | 7:30 AM |
| Darien | | |
| Fairfield Prep | | |
| Fairfield Ludlowe | | |
| Fairfield Warde | | |
| Greenwich | | |
| New Canaan | | |
| New Milford | | |
| Norwalk | | |
| Stamford | | |
| Staples | | |
| St. Joseph | | |
| Trumbull | | |
| Westhill | | |
| Wilton | | |
| WED 1/31 | 6:00 PM | Varsity | League | Normal | Away | Joel Barlow | | | | Joel Barlow High - Upper Gym | 4:30 PM |
| SAT 2/3 | 12:01 AM | Other | League | Normal | Away | Bunnell | | | | Fairfield Ludlowe High School - Main Gym | 7:45 AM |
| Fairfield Prep | | |
| Fairfield Ludlowe | | |
| Fairfield Warde | | |
| Greenwich | | |
| Norwalk | | |
| Shelton | | |
| Simsbury | | |
| Stamford | | |
| Stratford | | |
| MON 2/5 | 6:00 PM | Varsity | League | Normal | Away | New Milford | Loss | 12-72 | | New Milford High School - Small Gym - NMHS | 4:00 PM |