| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Away | East Lyme | | | | East Lyme High School - Rocky Neck State Park | 1:45 PM - 1 Bus |
| Plainfield | | |
| FRI 9/15 | 4:30 PM | Varsity | League | Normal | Away | Montville | | | | Wheeler Middle High School - MHS Gymatorium | 1:30 PM |
| Wheeler | | |
| | |
| Plainfield | | |
| Norwich Tech | | |
| Ellis Tech | | |
| Tourtellotte | | |
| TUE 9/19 | 4:30 PM | Varsity | League | Normal | Home | Stonington | | | | Lyman Memorial High School - Track | |
| FRI 9/29 | Canceled | Varsity | Non-League | Canceled | Away | South Windsor | | | | Nevers Road Park - Nevers Road Park XC Trail | 1:00 PM - 1 Bus |
| Windham | | |
| Avon | | |
| Hale Ray | | |
| Parish Hill | | |
| Bristol Central | | |
| Stafford | | |
| Bloomfield | | |
| University | | |
| East Hartford | | |
| Bristol Eastern | | |
| Northwest Catholic | | |
| Windsor | | |
| East Catholic | | |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Away | St. Bernard | | | | St. Bernard School - Track | 2:20 PM - 1 Bus |
| Tourtellotte | | |
| Wheeler | | |
| TUE 10/10 | 4:30 PM | Varsity | League | Normal | Home | Windham | | | | Lyman Memorial High School - Track | |
| Montville | | |
| FRI 10/13 | 4:00 PM | Varsity | Non-League | Normal | Away | South Windsor | | | | Nevers Road Park - Nevers Road Park XC Trail | |
| East Catholic | | |
| Bulkeley | | |
| Cromwell | | |
| Enfield | | |
| Windham | | |
| Avon | | |
| East Hartford | | |
| Parish Hill | | |
| RHAM | | |
| Hale Ray | | |
| Windsor | | |
| Norwich Tech | | |
| University | | |
| THU 10/19 | 1:30 PM | Varsity | Postseason | Normal | Away | St. Bernard | | | | Norwich Golf Course - Norwich Golf Course | 11:30 AM |
| Stonington | | |
| Ledyard | | |
| Bacon Academy | | |
| Waterford | | |
| Norwich Free Academy | | |
| East Lyme | | |
| Windham | | |
| Fitch | | |
| Tourtellotte | | |
| New London | | |
| Griswold | | |
| Woodstock Academy | | |
| Montville | | |
| Plainfield | | |
| Killingly | | |
| Putnam | | |
| Wheeler | | |