| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 9/14 | 3:45 PM | Varsity | League | Normal | Home | New Britain | | | | Bloomfield High School - Cross Country Course | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Away | Newington | | | | John Wallace MS - John Wallace MS | |
| FRI 9/29 | Canceled | Varsity | Non-League | Canceled | Away | East Catholic | | | | Nevers Road Park - Nevers Road Park XC Trail | |
| Lyman Memorial | | |
| Hale Ray | | |
| Parish Hill | | |
| Windham | | |
| Avon | | |
| Bristol Central | | |
| Stafford | | |
| Windsor | | |
| South Windsor | | |
| Bristol Eastern | | |
| East Hartford | | |
| Northwest Catholic | | |
| University | | |
| TUE 10/3 | 3:45 PM | Varsity | League | Normal | Away | Wethersfield | | | | Wethersfield Cove Park - Wethersfield Cove Park | |
| Rocky Hill | | |
| Hartford Public | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | Windsor | | | | Windsor High School - Northwest Park | |