| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:30 PM | Varsity | League | Normal | Away | Plainfield | | | | Plainfield High School Athletic Upper Complex - Cross Country Course | |
| St. Bernard | | |
| TUE 9/17 | 3:30 PM | Varsity | League | Normal | Home | Lyman Memorial | | | | St. Marie Greenhalgh Sports Complex - Nature Trail | |
| Windham | | |
| TUE 10/1 | 4:30 PM | Varsity | League | Normal | Away | Tourtellotte | | | | East Lyme High School | |
| East Lyme | | |
| New London | | |
| NFA | | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Away | Montville | | | | Wheeler Middle High School - MHS XC Course | |
| Fitch | | |
| Wheeler | | |
| Fishers Island High School | | |
| THU 10/17 | 1:30 PM | Varsity | Postseason | Normal | Away | Woodstock Academy | | | | Norwich Golf Course - Norwich Golf Course | |
| Wheeler | | |
| Windham | | |
| Waterford | | |
| Griswold | | |
| Killingly | | |
| Ledyard | | |
| Lyman Memorial | | |
| Montville | | |
| East Lyme | | |
| Fitch | | |
| Bacon Academy | | |
| New London | | |
| NFA | | |
| Stonington | | |
| Tourtellotte | | |
| Plainfield | | |
| St. Bernard | | |