| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:30 p.m. | Varsity | League | Normal | Home | Thomaston | | | | Housatonic Valley Regional High-Cross Country Course | |
| TUE 9/17 | 4:00 p.m. | Varsity | League | Normal | Away | Litchfield | | | | Plumb Hill Field Complex-Plumb Hill Track | |
| TUE 9/24 | 4:30 p.m. | Varsity | League | Normal | Home | Nonnewaug | | | | Housatonic Valley Regional High-Cross Country Course | |
| THU 9/26 | 4:00 p.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | YMCA Camp Sloper | |
| TUE 10/8 | 4:00 p.m. | Varsity | League | Normal | Away | Gilbert | | | | 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 | |