| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 9/14 | 4:45 PM | Varsity | League | Normal | Away | Granby Memorial | | | | Granby Memorial High School - XC Course | 2:30 PM |
| Rockville | | |
| Coventry | | |
| THU 9/21 | 4:00 PM | Varsity | League | Normal | Away | Somers | | | | Somers High School - P&R XC Course | 2:20 PM |
| Bolton | | |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Home | East Granby | | | | Suffield High School - Bruce Park | |
| Canton | | |
| WED 10/4 | 4:00 PM | Varsity | League | Normal | Home | Stafford | | | | Suffield High School - Bruce Park | |
| Windsor Locks | | |
| WED 10/11 | 4:00 PM | Varsity | League | Normal | Home | East Windsor | | | | Suffield High School - Bruce Park | |
| Ellington | | |
| WED 10/18 | 12:01 AM | Varsity | League | Normal | Away | Rockville | | | | Bolton High School - BHS Cross Country Course | 12:01 AM |
| Somers | | |
| Windsor Locks | | |
| East Windsor | | |
| Coventry | | |
| Bolton | | |
| East Granby | | |
| Ellington | | |
| | |
| Granby Memorial | | |
| Stafford | | |
| Canton | | |