| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/3 | 3:45 PM | Varsity | League | Normal | Away | Aerospace | | | | Elizabeth Park - Cross Country Course | 2:45 AM |
| Achievement First | | |
| Bulkeley | | |
| Capital Prep | | |
| Innovation | | |
| Classical Magnet | | |
| International | | |
| Parish Hill | | |
| Comp Sci | | |
| HMTCA | | |
| University | | |
| Weaver | | |
| FRI 9/13 | 3:30 PM | Varsity | Non-League | Normal | Away | University | | | | Nevers Road Park - Nevers Road Park XC Trail | 2:00 PM |
| Windham Tech | | |
| Windsor | | |
| South Windsor | | |
| Portland | | |
| Northwest Catholic | | |
| Norwich Tech | | |
| Ellis Tech | | |
| Lyman Memorial | | |
| East Catholic | | |
| East Hartford | | |
| East Windsor | | |
| Enfield | | |
| Bristol Central | | |
| Bristol Eastern | | |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | Achievement First | | | | Northwest Park - Cross Country Course | 2:45 PM |
| Aerospace | | |
| Capital Prep | | |
| Bulkeley | | |
| Classical Magnet | | |
| International | | |
| Innovation | | |
| Parish Hill | | |
| Comp Sci | | |
| Weaver | | |
| HMTCA | | |
| University | | |
| TUE 10/1 | 3:45 PM | Varsity | League | Normal | Away | University | | | | Elizabeth Park - Cross Country Course | 3:00 PM |
| HMTCA | | |
| Weaver | | |
| Comp Sci | | |
| Parish Hill | | |
| Innovation | | |
| International | | |
| Classical Magnet | | |
| Bulkeley | | |
| Capital Prep | | |
| Aerospace | | |
| Achievement First | | |
| TUE 10/8 | 3:45 PM | Varsity | League | Normal | Away | Aerospace | | | | Northwest Park - Cross Country Course | 3:00 PM |
| Achievement First | | |
| Bulkeley | | |
| Capital Prep | | |
| Classical Magnet | | |
| Innovation | | |
| International | | |
| Parish Hill | | |
| Comp Sci | | |
| Weaver | | |
| HMTCA | | |
| University | | |
| TUE 10/15 | 3:00 PM | Varsity | League | Normal | Away | University | | | | Stanley Quarter Park - Cross Country | 1:45 PM |
| HMTCA | | |
| Weaver | | |
| Comp Sci | | |
| Parish Hill | | |
| Classical Magnet | | |
| International | | |
| Innovation | | |
| Aerospace | | |
| Achievement First | | |
| Capital Prep | | |
| Bulkeley | | |