| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/1 | 3:45 PM | Varsity | Scrimmage | Normal | Away | Avon | | | | Cromwell High School - cross country course | |
| Hale Ray | | |
| Berlin | | |
| Cromwell | | |
| THU 9/14 | 4:45 PM | Varsity | League | Normal | Home | Coventry | | | | Granby Memorial High School - XC Course | |
| Rockville | | |
| Suffield | | |
| WED 9/20 | 3:30 PM | Varsity | League | Normal | Away | East Granby | | | | East Granby Farms - East Granby Farms | |
| WED 9/27 | 4:45 PM | Varsity | League | Normal | Away | Somers | | | | Ellington High School - Track | |
| Windsor Locks | | |
| Ellington | | |
| WED 10/4 | Canceled | Varsity | League | Canceled | Away | East Windsor | | | | East Windsor Senior High School - Track & Field | |
| WED 10/11 | 4:15 PM | Varsity | League | Normal | Away | Bolton | | | | Stratton Brook State Park - Stratton Brook State Park | |
| Stafford | | |
| Canton | | |
| WED 10/18 | 12:01 AM | Varsity | League | Normal | Away | Rockville | | | | Bolton High School - BHS Cross Country Course | |
| Coventry | | |
| East Windsor | | |
| | |
| Suffield | | |
| Bolton | | |
| Ellington | | |
| Windsor Locks | | |
| Stafford | | |
| East Granby | | |
| Canton | | |
| Somers | | |