| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:30 PM | Varsity | League | Normal | Home | Bacon Academy | | | | Haley Farm State Park - Haley Farm State Park | |
| NFA | | |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Home | Ledyard | Tied | 29-29 | | Haley Farm State Park - Haley Farm State Park | |
| SAT 9/21 | 9:30 AM | Varsity | Non-League | Normal | Away | | | | | Wrentham Development Center - Cross Country Course | 7:00 AM - 1 Bus |
| TUE 9/24 | 4:00 PM | Varsity | League | Normal | Home | East Lyme | | | | Haley Farm State Park - Haley Farm State Park | |
| SAT 9/28 | 12:15 PM | Varsity | Non-League | Normal | Away | | | | | Goddard Park - Goddard Park | 10:00 AM - 1 Bus |
| TUE 10/1 | 4:15 PM | Varsity | League | Normal | Away | Killingly | | | | Woodstock Fairgrounds - Woodstock Fairgrounds | |
| Woodstock Academy | | |
| Rectory School | | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Away | Fishers Island High School | | | | Wheeler Middle High School - MHS XC Course | |
| Putnam | | |
| Wheeler | | |
| Montville | | |
| THU 10/17 | 1:30 PM | Varsity | Postseason | Normal | Away | Montville | | | | Norwich Golf Course - Norwich Golf Course | 10:45 AM |
| New London | | |
| NFA | | |
| Lyman Memorial | | |
| Plainfield | | |
| Ledyard | | |
| Bacon Academy | | |
| East Lyme | | |
| Griswold | | |
| Killingly | | |
| Wheeler | | |
| Windham | | |
| Woodstock Academy | | |
| Putnam | | |
| St. Bernard | | |
| Stonington | | |
| Tourtellotte | | |
| Waterford | | |