| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 3:45 PM | Varsity | League | Normal | Away | Platt | | | | Hubbard Park - Tennis courts | |
| Plainville | | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Home | Berlin | | | | Rockwell Park - Cross Country Course | |
| Lewis Mills | | |
| FRI 9/29 | Canceled | Varsity | Non-League | Canceled | Away | Hall | | | | Nevers Road Park - Nevers Road Park XC Trail | |
| Ellis Tech | | |
| Hale Ray | | |
| East Catholic | | |
| Lyman Memorial | | |
| Parish Hill | | |
| Northwest Catholic | | |
| Bristol Eastern | | |
| Windham | | |
| Norwich Tech | | |
| Windsor | | |
| Stafford | | |
| South Windsor | | |
| East Hartford | | |
| University | | |
| Glastonbury | | |
| TUE 10/3 | 3:45 PM | Varsity | League | Normal | Away | Maloney | | | | Hubbard Park - Hubbard Park Band Shell | |
| Middletown | | |
| THU 10/12 | 3:45 PM | Varsity | League | Normal | Home | Bristol Eastern | | | | Rockwell Park - Cross Country Course | |
| St. Paul Catholic | | |