| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 3:45 PM | Varsity | League | Normal | Away | Comp Sci | | | | Colt Park - Cross Country Course | |
| Capital Prep | | |
| International | | |
| University | | |
| Aerospace | | |
| Bulkeley | | |
| Weaver | | |
| Innovation | | |
| | |
| Classical Magnet | | |
| HMTCA | | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Away | University | | | | Northwest Park - Northwest Park | |
| Comp Sci | | |
| Capital Prep | | |
| International | | |
| Bulkeley | | |
| HMTCA | | |
| Innovation | | |
| Weaver | | |
| Classical Magnet | | |
| | |
| Aerospace | | |
| WED 9/20 | 3:30 PM | Varsity | Non-League | Normal | Away | Housatonic Regional | | | | Coginchaug Regional High School - Coginchaug Regional HS | |
| East Hampton | | |
| Hale Ray | | |
| Coginchaug | | |
| Platt | | |
| New London | | |
| Avon | | |
| East Catholic | | |
| Old Saybrook | | |
| Maloney | | |
| Thomaston | | |
| Holy Cross | | |
| Valley Regional | | |
| Portland | | |
| Nonnewaug | | |
| TUE 9/26 | 3:45 PM | Varsity | League | Normal | Away | Bulkeley | | | | Elizabeth Park - Cross Country Course | |
| Comp Sci | | |
| University | | |
| International | | |
| Capital Prep | | |
| Classical Magnet | | |
| Innovation | | |
| Weaver | | |
| HMTCA | | |
| | |
| Aerospace | | |
| FRI 9/29 | Canceled | Varsity | Non-League | Canceled | Away | University | | | | Nevers Road Park - Nevers Road Park XC Trail | |
| Northwest Catholic | | |
| Hale Ray | | |
| Ellis Tech | | |
| Hall | | |
| Glastonbury | | |
| Norwich Tech | | |
| East Catholic | | |
| South Windsor | | |
| East Hartford | | |
| Stafford | | |
| Bristol Central | | |
| Windham | | |
| Bristol Eastern | | |
| Windsor | | |
| Lyman Memorial | | |
| TUE 10/3 | 3:45 PM | Varsity | League | Normal | Away | Innovation | | | | Northwest Park - Northwest Park | |
| International | | |
| University | | |
| Comp Sci | | |
| Capital Prep | | |
| HMTCA | | |
| Bulkeley | | |
| Weaver | | |
| Classical Magnet | | |
| | |
| Aerospace | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | University | | | | Colt Park - Cross Country Course | |
| Comp Sci | | |
| Capital Prep | | |
| International | | |
| Innovation | | |
| Aerospace | | |
| Bulkeley | | |
| Weaver | | |
| | |
| Classical Magnet | | |
| HMTCA | | |
| FRI 10/13 | 4:00 PM | Varsity | Non-League | Normal | Away | University | | | | Nevers Road Park - Nevers Road Park XC Trail | |
| East Hartford | | |
| Hale Ray | | |
| Enfield | | |
| Hall | | |
| Lyman Memorial | | |
| Bulkeley | | |
| Windham | | |
| Cromwell | | |
| Ellis Tech | | |
| Norwich Tech | | |
| Windsor | | |
| South Windsor | | |
| RHAM | | |
| East Catholic | | |
| TUE 10/17 | 3:45 PM | Varsity | League | Normal | Away | Innovation | | | | Elizabeth Park - Cross Country Course | |
| Comp Sci | | |
| University | | |
| International | | |
| Capital Prep | | |
| Classical Magnet | | |
| Bulkeley | | |
| Weaver | | |
| Aerospace | | |
| | |
| HMTCA | | |
| TUE 10/24 | 3:45 PM | Varsity | League | Normal | Away | University | | | | Elizabeth Park - Cross Country Course | |
| Comp Sci | | |
| Capital Prep | | |
| Weaver | | |
| Bulkeley | | |
| Classical Magnet | | |
| Innovation | | |
| International | | |
| HMTCA | | |
| Aerospace | | |
| | |