| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 4:30 PM | Varsity | League | Normal | Away | Wheeler | | | | Wheeler Middle High School - MHS Gymatorium | 12:00 PM |
| | |
| Tourtellotte | | |
| Putnam | | |
| TUE 9/19 | 4:30 PM | Varsity | League | Normal | Away | Tourtellotte | | | | Zagray Farm - Zagray Farm | |
| Bacon Academy | | |
| Waterford | | |
| WED 9/20 | 3:30 PM | Varsity | Non-League | Normal | Away | Thomaston | | | | Coginchaug Regional High School - Coginchaug Regional HS | |
| East Hampton | | |
| Avon | | |
| Hale Ray | | |
| East Catholic | | |
| Portland | | |
| Coginchaug | | |
| Platt | | |
| Nonnewaug | | |
| Maloney | | |
| Parish Hill | | |
| Old Saybrook | | |
| Holy Cross | | |
| Valley Regional | | |
| Housatonic Regional | | |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Away | Plainfield | | | | Montville High School - XC Course | |
| Stonington | | |
| Montville | | |
| TUE 10/10 | 4:00 PM | Varsity | League | Normal | Away | St. Bernard | | | | St. Bernard School - Track | |
| Stonington | | |
| Putnam | | |
| THU 10/19 | 1:30 PM | Varsity | Postseason | Normal | Away | Windham | | | | Norwich Golf Course - Norwich Golf Course | |
| Fitch | | |
| Norwich Free Academy | | |
| Woodstock Academy | | |
| Wheeler | | |
| Montville | | |
| St. Bernard | | |
| Putnam | | |
| East Lyme | | |
| Killingly | | |
| Tourtellotte | | |
| Lyman Memorial | | |
| Griswold | | |
| Bacon Academy | | |
| Plainfield | | |
| Stonington | | |
| Waterford | | |
| Ledyard | | |