| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/6 | Postponed | Varsity | League | Postponed | Away | Gilbert | | | | Thomaston High School - Black Rock State Park | 12:01 AM |
| Housatonic Regional | | |
| Litchfield | | |
| Nonnewaug | | |
| Northwestern | | |
| Shepaug Valley | | |
| Terryville | | |
| Thomaston | | |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Away | Housatonic Regional | | | | Housatonic Valley Regional High - Football Field/Game Soccer/Track/Cross Country Start & Finish | |
| Northwestern | | |
| SAT 9/30 | 10:00 AM | Varsity | Non-League | Normal | Away | Nonnewaug | | | | Nonnewaug High School - XC Course | 12:01 AM |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Away | Shepaug Valley | | | | Terryville High School - Track | |
| Terryville | | |
| TUE 10/10 | 3:00 PM | Varsity | League | Normal | Away | Litchfield | | | | Nonnewaug High School - XC Course | |
| Nonnewaug | | |
| THU 10/12 | 4:00 PM | Varsity | League | Normal | Home | Gilbert | | | | Wamogo Regional High School - White Memorial Park | |
| Thomaston | | |
| THU 10/19 | 2:45 PM | Varsity | Postseason | Normal | Away | Gilbert | | | | Thomaston High School - Black Rock State Park | |
| Housatonic Regional | | |
| Litchfield | | |
| Nonnewaug | | |
| Northwestern | | |
| Shepaug Valley | | |
| Terryville | | |
| Thomaston | | |