| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 3:45 PM | Varsity | League | Normal | Home | | | | | Colt Park - Cross Country Course | |
| Bulkeley | | |
| Capital Prep | | |
| Classical Magnet | | |
| Innovation | | |
| Parish Hill | | |
| International | | |
| Comp Sci | | |
| University | | |
| HMTCA | | |
| Weaver | | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Home | Weaver | | | | Northwest Park - Northwest Park | |
| University | | |
| HMTCA | | |
| Comp Sci | | |
| International | | |
| Parish Hill | | |
| Classical Magnet | | |
| Innovation | | |
| Bulkeley | | |
| Capital Prep | | |
| | |
| TUE 9/26 | 3:45 PM | Varsity | League | Normal | Home | | | | | Elizabeth Park - Cross Country Course | |
| Bulkeley | | |
| Capital Prep | | |
| Classical Magnet | | |
| Innovation | | |
| Parish Hill | | |
| International | | |
| Comp Sci | | |
| University | | |
| HMTCA | | |
| Weaver | | |
| TUE 10/3 | 3:45 PM | Varsity | League | Normal | Home | Weaver | | | | Northwest Park - Northwest Park | |
| HMTCA | | |
| University | | |
| Comp Sci | | |
| International | | |
| Parish Hill | | |
| Innovation | | |
| Classical Magnet | | |
| | |
| Capital Prep | | |
| Bulkeley | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Home | Bulkeley | | | | Colt Park - Cross Country Course | |
| Capital Prep | | |
| | |
| Classical Magnet | | |
| Innovation | | |
| Parish Hill | | |
| International | | |
| Comp Sci | | |
| University | | |
| HMTCA | | |
| Weaver | | |
| TUE 10/17 | 3:45 PM | Varsity | League | Normal | Home | Weaver | | | | Elizabeth Park - Cross Country Course | |
| University | | |
| HMTCA | | |
| Parish Hill | | |
| Comp Sci | | |
| International | | |
| Innovation | | |
| Capital Prep | | |
| | |
| Bulkeley | | |
| Classical Magnet | | |
| TUE 10/24 | 3:45 PM | Varsity | League | Normal | Home | Capital Prep | | | | Elizabeth Park - Cross Country Course | |
| Bulkeley | | |
| | |
| Classical Magnet | | |
| Innovation | | |
| Parish Hill | | |
| International | | |
| Comp Sci | | |
| University | | |
| HMTCA | | |
| Weaver | | |