| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 12/20 | 7:00 p.m. | Varsity | League | Normal | Home | WamogoReg | Loss | 43-57 | | Thomaston High School-Gym | |
| WED 12/21 | 5:30 p.m. | Varsity | League | Normal | Away | EmmettOBrienRVT | Loss | 36-41 | | Emmett O' Brien Reg Voc Tech School-Gym | |
| TUE 12/27 | 6:30 p.m. | Varsity | League | Normal | Away | Litchfield | Loss | 29-38 | | Litchfield High School-Gym | |
| WED 12/28 | 5:00 p.m. | Varsity | League | Normal | Away | EastHampton | Loss | 58-72 | | Litchfield High School | |
| WED 1/4 | 7:00 p.m. | Varsity | League | Normal | Home | Gilbert | Win | 50-45 | | Thomaston High School-Gym | |
| FRI 1/6 | 7:00 p.m. | Varsity | League | Normal | Away | Terryville | Win | 53-42 | | Terryville High School-Gym | |
| TUE 1/10 | 6:00 p.m. | Varsity | League | Normal | Away | Nonnewaug | Loss | 39-62 | | Nonnewaug High School-Gym | |
| THU 1/12 | 7:00 p.m. | Varsity | League | Normal | Home | WindsorLocks | Loss | 46-69 | | Thomaston High School-Gym | |
| FRI 1/13 | 7:00 p.m. | Varsity | League | Normal | Home | ShepaugValley | Loss | 78-47 | | Thomaston High School-Gym | |
| TUE 1/17 | 7:00 p.m. | Varsity | League | Normal | Home | HousatonicValleyReg | Win | 62-25 | | Thomaston High School-Gym | |
| WED 1/18 | 6:45 p.m. | Varsity | League | Normal | Away | OliverWolcottRVT | Win | 77-50 | | Oliver Wolcott Technical High School-Wolcott Tech Gym | |
| FRI 1/20 | 7:00 p.m. | Varsity | League | Normal | Away | NorthwesternReg | Loss | 57-64 | | Northwestern Regional H.S.-Main Gym | |
| TUE 1/24 | 7:00 p.m. | Varsity | League | Normal | Home | Litchfield | Loss | 46-51 | | Thomaston High School-Gym | |
| FRI 1/27 | 7:00 p.m. | Varsity | League | Normal | Away | WamogoReg | Loss | 41-55 | | Wamogo High School-Wamogo Large Gym | |
| TUE 1/31 | 6:30 p.m. | Varsity | League | Normal | Away | Gilbert | Loss | 43-59 | | Gilbert School-Gym | |
| TUE 2/7 | 7:00 p.m. | Varsity | League | Normal | Home | Nonnewaug | Loss | 56-70 | | Thomaston High School-Gym | |
| FRI 2/10 | 7:30 p.m. | Varsity | League | Normal | Home | Terryville | Win | 68-42 | | Thomaston High School-Gym | |
| TUE 2/14 | 7:00 p.m. | Varsity | League | Normal | Away | ShepaugValley | Loss | 52-53 | | Shepaug Valley High School-Ted Alex Gymnasium | |
| THU 2/16 | 7:00 p.m. | Varsity | League | Normal | Away | HousatonicValleyReg | Win | 76-49 | | Housatonic Valley Regional High-Edward S. Tyburski Gym | |
| FRI 2/24 | 5:00 p.m. | Varsity | League | Normal | Home | NorthwesternReg | Loss | 62-66 | | Thomaston High School-Gym | |