| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/11 | 4:00 PM | Varsity | League | Normal | Away | Rockville | | | | Suffield High School - Bruce Park | |
| Somers | | |
| Suffield | | |
| WED 9/18 | 4:45 PM | Varsity | League | Normal | Away | East Windsor | | | | Bolton High School - BHS Cross Country Course | |
| Bolton | | |
| WED 9/25 | 4:00 PM | Varsity | League | Normal | Home | Coventry | | | | Stratton Brook State Park - Stratton Brook State Park | |
| Ellington | | |
| WED 10/2 | 4:00 PM | Varsity | League | Normal | Home | East Granby | | | | Stratton Brook State Park - Stratton Brook State Park | |
| Windsor Locks | | |
| WED 10/9 | 4:15 PM | Varsity | League | Normal | Away | Granby Memorial | | | | Granby Memorial High School - XC Course | |
| Stafford | | |
| WED 10/16 | 3:45 PM | Varsity | Tournament | Normal | Away | Stafford | | | | Bolton High School - BHS Cross Country Course | |
| Suffield | | |
| SMSA | | |
| Ellington | | |
| Somers | | |
| Granby Memorial | | |
| Rockville | | |
| East Granby | | |
| East Windsor | | |
| Coventry | | |
| Windsor Locks | | |
| Bolton | | |