| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 3:45 PM | Varsity | League | Normal | Away | Southington | | | | Stratton Brook State Park - Stratton Brook State Park | 1:15 PM |
| Simsbury | | |
| TUE 9/19 | 4:00 PM | Varsity | League | Normal | Home | Farmington | | | | Hall High School - Stadium (Track) | |
| Glastonbury | | |
| FRI 9/29 | Canceled | Varsity | Non-League | Canceled | Away | Bristol Central | | | | Nevers Road Park - Nevers Road Park XC Trail | 1:15 PM |
| Parish Hill | | |
| Stafford | | |
| Glastonbury | | |
| South Windsor | | |
| East Catholic | | |
| Bristol Eastern | | |
| Hale Ray | | |
| Ellis Tech | | |
| University | | |
| East Hartford | | |
| Norwich Tech | | |
| Lyman Memorial | | |
| Northwest Catholic | | |
| Windham | | |
| Windsor | | |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Home | Avon | | | | Hall High School - Stadium (Track) | |
| Northwest Catholic | | |
| WED 10/11 | 3:45 PM | Varsity | League | Normal | Away | Conard | | | | Reservoir Rt. 4 - Reservoir Rt. 4 | 2:45 PM |
| FRI 10/13 | 4:00 PM | Varsity | Non-League | Normal | Away | Bulkeley | | | | Nevers Road Park - Nevers Road Park XC Trail | 1:15 PM |
| Norwich Tech | | |
| Cromwell | | |
| Windham | | |
| Parish Hill | | |
| Enfield | | |
| University | | |
| Windsor | | |
| RHAM | | |
| Ellis Tech | | |
| East Catholic | | |
| Lyman Memorial | | |
| Hale Ray | | |
| South Windsor | | |
| East Hartford | | |