| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 3:45 PM | Varsity | League | Normal | Home | Enfield | | | | Wickham Park - Wickham Park | |
| Tolland | | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Away | South Windsor | | | | Mansfield Hollow State Park - Boys Course | |
| E.O. Smith | | |
| TUE 9/26 | 3:45 PM | Varsity | League | Normal | Away | East Catholic | | | | Wickham Park - Wickham Park | |
| RHAM | | |
| FRI 9/29 | Canceled | Varsity | Non-League | Canceled | Away | Norwich Tech | | | | Nevers Road Park - Nevers Road Park XC Trail | |
| Parish Hill | | |
| Glastonbury | | |
| Bristol Central | | |
| South Windsor | | |
| Ellis Tech | | |
| Hale Ray | | |
| Windham | | |
| University | | |
| Stafford | | |
| Bristol Eastern | | |
| Windsor | | |
| Lyman Memorial | | |
| East Catholic | | |
| Northwest Catholic | | |
| Hall | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Home | Manchester | | | | Wickham Park - Wickham Park | |
| FRI 10/13 | 4:00 PM | Varsity | Non-League | Normal | Away | Bulkeley | | | | Nevers Road Park - Nevers Road Park XC Trail | |
| Windsor | | |
| Cromwell | | |
| Parish Hill | | |
| Norwich Tech | | |
| Hall | | |
| University | | |
| Ellis Tech | | |
| South Windsor | | |
| Windham | | |
| Hale Ray | | |
| Enfield | | |
| Lyman Memorial | | |
| RHAM | | |
| East Catholic | | |