| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 3:45 PM | Varsity | League | Normal | Away | Valley Regional | | | | Indian River Complex - XC Course | 2:55 PM |
| Old Lyme | | |
| Morgan | | |
| WED 9/20 | 3:30 PM | Varsity | Non-League | Normal | Away | Nonnewaug | | | | Coginchaug Regional High School - Coginchaug Regional HS | 2:15 PM |
| Maloney | | |
| New London | | |
| Hale Ray | | |
| Parish Hill | | |
| Thomaston | | |
| Valley Regional | | |
| Platt | | |
| Portland | | |
| Avon | | |
| East Hampton | | |
| Coginchaug | | |
| Holy Cross | | |
| East Catholic | | |
| Housatonic Regional | | |
| THU 10/12 | 3:30 PM | Varsity | Scrimmage | Normal | Home | Old Lyme | | | | Old Saybrook High School - Old Saybrook Campus | |