| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Home | Killingly | | | | Montville High School - XC Course | |
| St. Bernard | | |
| FRI 9/15 | 4:00 PM | Varsity | League | Normal | Away | Norwich Tech | | | | Wheeler Middle High School - MHS Gymatorium | |
| Lyman Memorial | | |
| Plainfield | | |
| Tourtellotte | | |
| Wheeler | | |
| Ellis Tech | | |
| | |
| TUE 9/19 | 4:00 PM | Varsity | League | Normal | Away | Woodstock Academy | | | | East Lyme High School - Rocky Neck State Park | |
| East Lyme | | |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Home | Stonington | | | | Montville High School - XC Course | |
| Plainfield | | |
| New London | | |
| TUE 10/10 | 4:30 PM | Varsity | League | Normal | Away | Windham | | | | Lyman Memorial High School - Track | |
| Lyman Memorial | | |
| THU 10/19 | 1:30 PM | Varsity | Postseason | Normal | Away | St. Bernard | | | | Norwich Golf Course - Norwich Golf Course | |
| Griswold | | |
| Stonington | | |
| Waterford | | |
| East Lyme | | |
| Lyman Memorial | | |
| Putnam | | |
| Killingly | | |
| Ledyard | | |
| Fitch | | |
| Norwich Free Academy | | |
| Windham | | |
| Woodstock Academy | | |
| New London | | |
| Wheeler | | |
| Bacon Academy | | |
| Tourtellotte | | |
| Plainfield | | |