| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | New London | | | | Wheeler Middle High School - MHS XC Course | |
| Plainfield | | |
| TUE 9/24 | 4:30 PM | Varsity | League | Normal | Away | Killingly | | | | Stonington High School - Palmer Field (Turf Stadium) | 3:00 PM |
| Stonington | | |
| TUE 10/1 | 5:15 PM | Varsity | League | Normal | Away | Lyman Memorial | | | | St. Bernard School - Track | 3:00 PM |
| St. Bernard | | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Home | Putnam | | | | Wheeler Middle High School - MHS XC Course | |
| Montville | | |
| Fitch | | |
| Fishers Island High School | | |
| FRI 10/11 | 3:00 PM | Varsity | Non-League | Normal | Away | Fishers Island High School | | | | Fishers Island High School | 11:30 AM |
| THU 10/17 | 1:30 PM | Varsity | Postseason | Normal | Away | Tourtellotte | | | | Norwich Golf Course - Norwich Golf Course | |
| Waterford | | |
| Windham | | |
| Woodstock Academy | | |
| Griswold | | |
| Killingly | | |
| Bacon Academy | | |
| East Lyme | | |
| Fitch | | |
| Montville | | |
| Ledyard | | |
| Lyman Memorial | | |
| Putnam | | |
| St. Bernard | | |
| Stonington | | |
| Plainfield | | |
| New London | | |
| NFA | | |