| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/3 | 4:00 PM | Varsity | Scrimmage | Normal | Away | Gilbert | | | | Thomaston High School - Black Rock State Park | |
| Housatonic Regional | | |
| Lakeview | | |
| Nonnewaug | | |
| Northwestern | | |
| Shepaug Valley | | |
| Thomaston | | |
| TUE 9/10 | 4:00 PM | Varsity | League | Normal | Home | Lakeview | | | | Terryville High School - Track | |
| Housatonic Regional | | |
| TUE 9/24 | 4:00 PM | Varsity | League | Normal | Away | Shepaug Valley | | | | Shepaug Valley High School - Shepaug Valley Middle & High School Cross Country Course | |
| TUE 10/1 | 3:45 PM | Varsity | League | Normal | Home | Northwestern | | | | Terryville High School - Track | |
| Gilbert | | |
| TUE 10/8 | 3:45 PM | Varsity | League | Normal | Away | Nonnewaug | | | | Nonnewaug High School - XC Course | |
| Thomaston | | |
| THU 10/17 | 2:45 PM | Varsity | League | Normal | Away | Thomaston | | | | Black Rock State Park - Black Rock State Park | |
| Nonnewaug | | |
| Northwestern | | |
| Shepaug Valley | | |
| | |
| Gilbert | | |
| Lakeview | | |