| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 3:45 PM | Varsity | League | Normal | Away | Vinal Tech | | | | Vinal Tech - Vinal CC Course | |
| Windham Tech | | |
| FRI 9/15 | 4:00 PM | Varsity | League | Normal | Away | Ellis Tech | | | | Wheeler Middle High School - MHS Gymatorium | |
| Lyman Memorial | | |
| Montville | | |
| Plainfield | | |
| Tourtellotte | | |
| Wheeler | | |
| | |
| TUE 9/19 | 4:00 PM | Varsity | League | Normal | Home | Grasso Tech | | | | Norwich Technical High School - Mohegan Park | |
| Cheney Tech | | |
| | |
| TUE 9/26 | 4:00 PM | Varsity | League | Normal | Away | Cheney Tech | | | | Cheney Tech. - Wickham Park | |
| FRI 9/29 | Canceled | Varsity | Non-League | Canceled | Away | Bristol Central | | | | Nevers Road Park - Nevers Road Park XC Trail | |
| Bristol Eastern | | |
| East Catholic | | |
| East Hartford | | |
| Glastonbury | | |
| Ellis Tech | | |
| Lyman Memorial | | |
| Hale Ray | | |
| Northwest Catholic | | |
| Parish Hill | | |
| South Windsor | | |
| Stafford | | |
| University | | |
| Windham | | |
| Windsor | | |
| Hall | | |
| TUE 10/3 | 3:45 PM | Varsity | League | Normal | Away | Prince Tech | | | | Vinal Tech - Vinal CC Course | |
| Vinal Tech | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | Ellis Tech | | | | Owen Bell Park - X-C Course | |
| FRI 10/13 | 4:00 PM | Varsity | Non-League | Normal | Away | Bulkeley | | | | Nevers Road Park - Nevers Road Park XC Trail | |
| Cromwell | | |
| East Catholic | | |
| East Hartford | | |
| Enfield | | |
| Ellis Tech | | |
| Lyman Memorial | | |
| Hale Ray | | |
| Parish Hill | | |
| RHAM | | |
| South Windsor | | |
| University | | |
| Windham | | |
| Windsor | | |
| Hall | | |
| MON 10/16 | 2:00 PM | Varsity | Postseason | Normal | Away | Prince Tech | | | | Wickham Park - Manchester, Ct | |
| Bullard Havens Tech | | |
| Grasso Tech | | |
| Ellis Tech | | |
| Wilcox Tech | | |
| Abbott Tech | | |
| Cheney Tech | | |
| Wright Tech | | |
| Wolcott Tech | | |
| Platt Tech | | |
| Vinal Tech | | |
| Kaynor Tech | | |
| Windham Tech | | |