| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/14 | 4:00 p.m. | Varsity | League | Normal | Away | Nonnewaug | | | | Nonnewaug High School-XC Course | |
| WED 9/22 | 4:00 p.m. | Varsity | League | Normal | Away | Terryville | | | | Terryville High School-Track | |
| THU 9/30 | 4:00 p.m. | Varsity | League | Normal | Home | NorthwesternReg | | | | Housatonic Valley Regional High-Cross Country Course | |
| TUE 10/12 | 5:00 p.m. | Varsity | League | Normal | Away | WamogoReg | | | | Wamogo Regional High School-White Memorial Park | |
| THU 10/21 | 4:15 p.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | Black Rock State Park | |