| 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 | |
| Thomaston | | |
| Terryville | | |
| Litchfield | | |
| Housatonic Regional | | |
| Gilbert | | |
| Shepaug Valley | | |
| Wamogo | | |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Away | Terryville | | | | Thomaston High School - Black Rock State Park | |
| Thomaston | | |
| WED 9/20 | 3:30 PM | Varsity | Non-League | Normal | Away | Thomaston | | | | Coginchaug Regional High School - Coginchaug Regional HS | |
| New London | | |
| Old Saybrook | | |
| Valley Regional | | |
| Avon | | |
| Holy Cross | | |
| East Catholic | | |
| East Hampton | | |
| Housatonic Regional | | |
| Maloney | | |
| Coginchaug | | |
| Hale Ray | | |
| Platt | | |
| Parish Hill | | |
| Portland | | |
| TUE 9/26 | 3:45 PM | Varsity | League | Normal | Home | Shepaug Valley | | | | Nonnewaug High School - XC Course | |
| Northwestern | | |
| SAT 9/30 | 10:00 AM | Varsity | Non-League | Normal | Home | Wamogo | | | | Nonnewaug High School - XC Course | |
| SAT 9/30 | 10:00 AM | Varsity | Non-League | Normal | Home | Torrington | | | | Nonnewaug High School - XC Course | |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Away | Gilbert | | | | Gilbert School - Cross Country | |
| Housatonic Regional | | |
| TUE 10/10 | 3:00 PM | Varsity | League | Normal | Home | Wamogo | | | | Nonnewaug High School - XC Course | |
| Litchfield | | |
| THU 10/19 | 2:45 PM | Varsity | Postseason | Normal | Away | Litchfield | | | | Thomaston High School - Black Rock State Park | |
| Terryville | | |
| Northwestern | | |
| Thomaston | | |
| Wamogo | | |
| Gilbert | | |
| Shepaug Valley | | |
| Housatonic Regional | | |