| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/6 | Postponed | Varsity | League | Postponed | Away | Nonnewaug | | | | Thomaston High School - Black Rock State Park | 2:25 PM |
| Gilbert | | |
| Housatonic Regional | | |
| Wamogo | | |
| Terryville | | |
| Litchfield | | |
| Thomaston | | |
| Northwestern | | |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Home | Gilbert | | | | Shepaug Valley High School - Shepaug Valley Middle & High School Cross Country Course | |
| Litchfield | | |
| TUE 9/26 | 3:45 PM | Varsity | League | Normal | Away | Nonnewaug | | | | Nonnewaug High School - XC Course | 2:25 PM |
| Northwestern | | |
| THU 9/28 | 4:00 PM | Varsity | League | Normal | Away | Kaynor Tech | | | | Black Rock State Park - Black Rock State Park | 2:25 PM |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Away | Wamogo | | | | Terryville High School - Track | 1:45 PM |
| Terryville | | |
| TUE 10/10 | 4:00 PM | Varsity | League | Normal | Away | Housatonic Regional | | | | Housatonic Valley Regional High - Football Field/Game Soccer/Track/Cross Country Start & Finish | 2:00 PM |
| Thomaston | | |
| THU 10/19 | 2:45 PM | Varsity | Postseason | Normal | Away | Gilbert | | | | Thomaston High School - Black Rock State Park | 12:25 PM |
| Housatonic Regional | | |
| Northwestern | | |
| Thomaston | | |
| Litchfield | | |
| Terryville | | |
| Wamogo | | |
| Nonnewaug | | |