| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/27 | 3:45 PM | Varsity | League | Normal | Away | Farmington | | | | Winding Trails - Cross Country Course | |
| Simsbury | | |
| FRI 9/29 | Canceled | Varsity | Non-League | Canceled | Away | East Hartford | | | | Nevers Road Park - Nevers Road Park XC Trail | |
| Windham | | |
| Glastonbury | | |
| Stafford | | |
| Ellis Tech | | |
| Bristol Central | | |
| Hall | | |
| University | | |
| Lyman Memorial | | |
| Windsor | | |
| Parish Hill | | |
| Norwich Tech | | |
| Hale Ray | | |
| Bristol Eastern | | |
| South Windsor | | |
| East Catholic | | |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Away | Hall | | | | Hall High School - Stadium (Track) | |
| Avon | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | Southington | | | | Southington High School - SHS | |
| FRI 10/13 | 4:00 PM | Varsity | League | Normal | Away | Conard | | | | JB Williams Park - JB Williams Park | |
| Glastonbury | | |