| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/14 | 4:00 p.m. | Varsity | League | Normal | Home | Terryville | | | | Northwestern Regional H.S.-Track | |
| TUE 9/21 | 4:00 p.m. | Varsity | League | Normal | Away | Thomaston | | | | Black Rock State Park | |
| THU 9/30 | 4:00 p.m. | Varsity | League | Normal | Away | HousatonicValleyReg | | | | Housatonic Valley Regional High-Cross Country Course | |
| TUE 10/12 | 4:00 p.m. | Varsity | League | Normal | Away | ShepaugValley | | | | Shepaug Valley High School-Shepaug Valley Middle & High School Cross Country Course | |
| THU 10/21 | 4:15 p.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | Black Rock State Park | |