| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 12/19 | 5:00 p.m. | Varsity | League | Normal | Home | Terryville | Loss | 47-94 | | Housatonic Valley Regional High-Gym | |
| FRI 12/20 | 7:00 p.m. | Varsity | League | Normal | Away | OliverWolcottRVT | Loss | 38-51 | | Oliver Wolcott Technical High School-Gym | |
| THU 1/2 | 7:00 p.m. | Varsity | League | Normal | Away | Litchfield | Loss | 40-64 | | Litchfield High School-Gym | |
| FRI 1/3 | 7:00 p.m. | Varsity | League | Normal | Home | ShepaugValley | Loss | 40-94 | | Housatonic Valley Regional High-Gym | |
| TUE 1/7 | 7:00 p.m. | Varsity | League | Normal | Away | NorthwesternReg | Loss | 31-67 | | Northwestern Regional H.S.-Main Gym | |
| FRI 1/10 | 6:00 p.m. | Varsity | League | Normal | Home | MtEverett | Win | 51-45 | | Housatonic Valley Regional High-Gym | |
| TUE 1/14 | 7:00 p.m. | Varsity | League | Normal | Home | Gilbert | Loss | 65-99 | | Housatonic Valley Regional High-Gym | |
| FRI 1/17 | 6:00 p.m. | Varsity | League | Normal | Away | Nonnewaug | Loss | 38-83 | | Nonnewaug High School-Gym | |
| TUE 1/21 | 7:00 p.m. | Varsity | League | Normal | Home | WamogoReg | Loss | 41-84 | | Housatonic Valley Regional High-Gym | |
| FRI 1/24 | 7:00 p.m. | Varsity | League | Normal | Away | Thomaston | Loss | 27-57 | | Thomaston High School-Gym | |
| TUE 1/28 | 7:00 p.m. | Varsity | League | Normal | Away | Terryville | Loss | 39-77 | | Terryville High School-Gym | |
| FRI 1/31 | 7:00 p.m. | Varsity | League | Normal | Home | Litchfield | Loss | 27-81 | | Housatonic Valley Regional High-Gym | |
| TUE 2/4 | 7:00 p.m. | Varsity | League | Normal | Away | ShepaugValley | Loss | 52-91 | | Shepaug Valley High School-Ted Alex Gymnasium | |
| FRI 2/7 | 7:00 p.m. | Varsity | League | Normal | Home | NorthwesternReg | Loss | 39-74 | | Housatonic Valley Regional High-Gym | |
| MON 2/10 | 7:00 p.m. | Varsity | League | Normal | Home | LewisMills | Loss | 42-80 | | Housatonic Valley Regional High-Gym | |
| TUE 2/11 | 7:00 p.m. | Varsity | League | Normal | Away | Gilbert | Loss | 58-78 | | Gilbert School-Gym | |
| WED 2/19 | 6:00 p.m. | Varsity | League | Normal | Home | Nonnewaug | Loss | 45-89 | | Housatonic Valley Regional High-Gym | |
| THU 2/20 | 7:00 p.m. | Varsity | League | Normal | Away | WamogoReg | Loss | 48-79 | | Wamogo High School-Wamogo Large Gym | |
| MON 2/24 | 7:00 p.m. | Varsity | League | Normal | Home | Thomaston | Loss | 68-95 | | Housatonic Valley Regional High-Gym | |
| WED 2/26 | 7:00 p.m. | Varsity | League | Normal | Home | OliverWolcottRVT | Win | 61-46 | | Housatonic Valley Regional High-Gym | |