| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 10/2 | 4:00 p.m. | Varsity | League | Normal | Home | NorthwesternReg | | | | Gilbert School-Cross Country | |
| THU 10/8 | 4:00 p.m. | Varsity | League | Normal | Away | Litchfield | | | | Plumb Hill Field Complex-Plumb Hill Track | |
| FRI 10/9 | 4:00 p.m. | Varsity | League | Normal | Home | WamogoReg | | | | Gilbert School-Cross Country | |
| WED 10/14 | 4:00 p.m. | Varsity | League | Normal | Away | HousatonicValleyReg | | | | Housatonic Valley Regional High-Cross Country Course | |
| MON 10/19 | 4:00 p.m. | Varsity | League | Normal | Away | ShepaugValley | | | | Shepaug Valley High School-Shepaug Valley Middle & High School Cross Country Course | |
| THU 10/22 | 4:00 p.m. | Varsity | League | Normal | Home | Nonnewaug | | | | Gilbert School-Cross Country | |
| FRI 10/23 | 4:00 p.m. | Varsity | League | Normal | Away | OliverWolcottRVT | | | | John Minetto State Park | |
| TUE 10/27 | 4:00 p.m. | Varsity | League | Normal | Home | Thomaston | | | | Gilbert School-Cross Country | |
| THU 11/5 | 4:00 p.m. | Varsity | League | Normal | Home | Terryville | | | | Gilbert School-Cross Country | |