| 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 | |
| Achievement First | | |
| Bulkeley | | |
| Capital Prep | | |
| Classical Magnet | | |
| Hartford Public | | |
| Innovation | | |
| International | | |
| Comp Sci | | |
| HMTCA | | |
| University | | |
| Weaver | | |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | Weaver | | | | Northwest Park - Cross Country Course | |
| HMTCA | | |
| University | | |
| International | | |
| Comp Sci | | |
| Innovation | | |
| Hartford Public | | |
| Capital Prep | | |
| Classical Magnet | | |
| Bulkeley | | |
| Aerospace | | |
| Achievement First | | |
| THU 9/19 | 3:45 PM | Varsity | Non-League | Normal | Home | Windham Tech | | | | Parish Hill High School - Cross Country Course | |
| TUE 10/1 | 3:45 PM | Varsity | League | Normal | Away | Weaver | | | | Elizabeth Park - Cross Country Course | |
| Comp Sci | | |
| International | | |
| University | | |
| HMTCA | | |
| Achievement First | | |
| Aerospace | | |
| Bulkeley | | |
| Classical Magnet | | |
| Hartford Public | | |
| Innovation | | |
| Capital Prep | | |
| TUE 10/8 | 3:45 PM | Varsity | League | Normal | Away | Classical Magnet | | | | Northwest Park - Cross Country Course | |
| Hartford Public | | |
| Innovation | | |
| Bulkeley | | |
| Capital Prep | | |
| Aerospace | | |
| Achievement First | | |
| HMTCA | | |
| International | | |
| Comp Sci | | |
| University | | |
| Weaver | | |
| TUE 10/15 | 3:00 PM | Varsity | League | Normal | Away | Weaver | | | | Stanley Quarter Park - Cross Country | |
| International | | |
| Comp Sci | | |
| University | | |
| HMTCA | | |
| Achievement First | | |
| Aerospace | | |
| Capital Prep | | |
| Bulkeley | | |
| Innovation | | |
| Hartford Public | | |
| Classical Magnet | | |