| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 10/2 | 4:00 p.m. | Varsity | League | Normal | Away | Thomaston | | | | Black Rock State Park | |
| TUE 10/6 | 4:00 p.m. | Varsity | League | Normal | Home | Terryville | | | | Nonnewaug High School-XC Course | |
| FRI 10/9 | 4:00 p.m. | Varsity | League | Normal | Away | NorthwesternReg | | | | Northwestern Regional H.S.-Track | |
| TUE 10/13 | 4:00 p.m. | Varsity | League | Normal | Away | Litchfield | | | | Plumb Hill Field Complex-Plumb Hill Track | |
| THU 10/22 | 4:00 p.m. | Varsity | League | Normal | Away | Gilbert | | | | Gilbert School-Cross Country | |
| FRI 10/23 | 4:00 p.m. | Varsity | League | Normal | Home | ShepaugValley | | | | Nonnewaug High School-XC Course | |
| MON 10/26 | 4:00 p.m. | Varsity | League | Normal | Home | WamogoReg | | | | Nonnewaug High School-XC Course | |
| TUE 10/27 | 4:00 p.m. | Varsity | League | Normal | Away | HousatonicValleyReg | | | | Housatonic Valley Regional High-Cross Country Course | |