| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 9/9 | 3:15 PM | Varsity | League | Normal | Home | Ellis Tech | | | | Windham Technical High School - Mansfield Hollow | |
| FRI 9/13 | 3:30 PM | Varsity | Non-League | Normal | Away | Ellis Tech | | | | Nevers Road Park - Nevers Road Park XC Trail | |
| Hartford Public | | |
| Lyman Memorial | | |
| Northwest Catholic | | |
| Bristol Central | | |
| Bristol Eastern | | |
| East Catholic | | |
| East Hartford | | |
| East Windsor | | |
| Enfield | | |
| Norwich Tech | | |
| Portland | | |
| South Windsor | | |
| University | | |
| Windsor | | |
| THU 9/19 | 3:45 PM | Varsity | Non-League | Normal | Away | Parish Hill | | | | Parish Hill High School - Cross Country Course | |
| FRI 9/20 | 3:45 PM | Varsity | League | Normal | Away | Grasso Tech | Loss | 25-33 | | Grasso Tech - Haley Farm | |
| TUE 9/24 | 3:45 PM | Varsity | League | Normal | Home | Norwich Tech | | | | Windham Technical High School - Mansfield Hollow | |
| FRI 9/27 | 3:45 PM | Varsity | League | Normal | Home | Prince Tech | | | | Windham Technical High School - Mansfield Hollow | |
| TUE 10/8 | 3:45 PM | Varsity | League | Normal | Home | Vinal Tech | | | | Windham Technical High School - Mansfield Hollow | |
| WED 10/16 | 3:00 PM | Varsity | Postseason | Normal | Away | Vinal Tech | | | | Wickham Park - Manchester, Ct | |
| Kaynor Tech | | |
| Wolcott Tech | | |
| Platt Tech | | |
| Prince Tech | | |
| Bullard Havens Tech | | |
| Grasso Tech | | |
| Norwich Tech | | |
| Ellis Tech | | |
| Wilcox Tech | | |
| Abbott Tech | | |
| Cheney Tech | | |
| Wright Tech | | |