| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Away | Montville | | | | Montville High School - XC Course | 2:15 PM - 1 Bus |
| St. Bernard | | |
| TUE 9/19 | 4:30 PM | Varsity | League | Normal | Away | Ledyard | | | | Plainfield High School Athletic Upper Complex - Cross Country Course | 3:15 PM - 1 Bus |
| Plainfield | | |
| Putnam | | |
| TUE 10/3 | 4:30 PM | Varsity | League | Normal | Home | Waterford | | | | Owen Bell Park - Softball Field | |
| TUE 10/10 | 4:00 PM | Varsity | League | Normal | Away | Bacon Academy | | | | Griswold High School - Hopeville State Park | 2:00 PM - 1 Bus |
| Griswold | | |
| THU 10/19 | 1:30 PM | Varsity | Postseason | Normal | Away | Bacon Academy | | | | Norwich Golf Course - Norwich Golf Course | 11:15 AM - Share w/ Girls |
| East Lyme | | |
| Fitch | | |
| Griswold | | |
| Ledyard | | |
| Lyman Memorial | | |
| Montville | | |
| New London | | |
| Norwich Free Academy | | |
| Plainfield | | |
| Putnam | | |
| St. Bernard | | |
| Stonington | | |
| Tourtellotte | | |
| Waterford | | |
| Wheeler | | |
| Windham | | |
| Woodstock Academy | | |