| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:00 p.m. | Varsity | League | Normal | Away | Nonnewaug | | | | Nonnewaug High-XC Course | |
| TUE 9/17 | 3:45 p.m. | Varsity | League | Normal | Away | WamogoReg | | | | Wamogo Regional High School-White Memorial Park | |
| TUE 9/24 | 4:00 p.m. | Varsity | League | Normal | Away | Thomaston | | | | Thomaston High School-Highwoods field | |
| TUE 10/8 | 4:00 p.m. | Varsity | League | Normal | Home | HousatonicValleyReg | | | | Gilbert School-Football Field | |
| FRI 10/18 | 4:15 p.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | Thomaston High School-Highwoods field | |