| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/17 | 4:30 PM | Varsity | League | Normal | Away | Montville | | | | Montville High School - XC Course | |
| St. Bernard | | |
| TUE 10/1 | 4:30 PM | Varsity | League | Normal | Away | East Lyme | | | | East Lyme High School - Rocky Neck State Park | |
| New London | | |
| Norwich Free Academy | | |
| Putnam | | |
| TUE 10/8 | 4:30 PM | Varsity | League | Normal | Away | Lyman Memorial | | | | Plainfield High School Athletic Upper Complex - Cross Country Course | |
| Plainfield | | |