| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/15 | 4:00 PM | Varsity | League | Normal | Away | East Granby | | | | East Granby Farms - East Granby Farms | 2:15 PM - 1 Bus |
| East Windsor | | |
| Somers | | |
| TUE 9/19 | 4:15 PM | Varsity | League | Normal | Home | Rockville | | | | Stafford High School - Track located behind the school | |
| Ellington | | |
| WED 9/27 | 4:15 PM | Varsity | League | Normal | Home | Coventry | | | | Stafford High School - Track located behind the school | |
| FRI 9/29 | Canceled | Varsity | Non-League | Canceled | Away | Avon | | | | Nevers Road Park - Nevers Road Park XC Trail | 2:15 PM - 1 Bus |
| Bloomfield | | |
| Bristol Central | | |
| Bristol Eastern | | |
| East Hartford | | |
| East Catholic | | |
| Lyman Memorial | | |
| Hale Ray | | |
| Northwest Catholic | | |
| Parish Hill | | |
| University | | |
| Windham | | |
| Windsor | | |
| South Windsor | | |
| WED 10/4 | 4:00 PM | Varsity | League | Normal | Away | Suffield | | | | Suffield High School - Bruce Park | 2:30 PM - 1 Bus |
| Windsor Locks | | |
| WED 10/11 | 4:15 PM | Varsity | League | Normal | Away | Granby Memorial | | | | Stratton Brook State Park - Stratton Brook State Park | 2:15 PM - 1 Bus |
| Bolton | | |
| Canton | | |
| WED 10/18 | 12:01 AM | Varsity | League | Normal | Away | Coventry | | | | Bolton High School - BHS Cross Country Course | 12:00 PM |
| Canton | | |
| Bolton | | |
| East Granby | | |
| East Windsor | | |
| Ellington | | |
| Granby Memorial | | |
| Somers | | |
| Rockville | | |
| | |
| Suffield | | |
| Windsor Locks | | |