| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/6 | Postponed | Varsity | League | Postponed | Away | Northwestern | | | | Thomaston High School - Black Rock State Park | |
| Housatonic Regional | | |
| Terryville | | |
| Wamogo | | |
| Thomaston | | |
| Litchfield | | |
| Shepaug Valley | | |
| Nonnewaug | | |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Away | Shepaug Valley | | | | Shepaug Valley High School - Shepaug Valley Middle & High School Cross Country Course | |
| Litchfield | | |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Home | Housatonic Regional | | | | Gilbert School - Cross Country | |
| Nonnewaug | | |
| TUE 10/10 | 4:00 PM | Varsity | League | Normal | Away | Terryville | | | | Northwestern Regional H.S. - Track | |
| Northwestern | | |
| THU 10/12 | 4:00 PM | Varsity | League | Normal | Away | Wamogo | | | | Wamogo Regional High School - White Memorial Park | |
| Thomaston | | |
| THU 10/19 | 2:45 PM | Varsity | Postseason | Normal | Away | Housatonic Regional | | | | Thomaston High School - Black Rock State Park | |
| Thomaston | | |
| Wamogo | | |
| Northwestern | | |
| Litchfield | | |
| Terryville | | |
| Shepaug Valley | | |
| Nonnewaug | | |