| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/11 | 4:00 PM | Varsity | League | Normal | Away | Career Magnet | | | | Sheehan High School - Sheehan HS Cross Country Course | |
| Hillhouse | | |
| Sheehan | | |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Away | Cheshire | | | | Cheshire Park - Field 1 | |
| Daniel Hand | | |
| East Haven | | |
| MON 9/23 | 4:00 PM | Varsity | Non-League | Normal | Away | East Haven | | | | Eisenhower Park - Eisenhower Park | |
| Jonathan Law | | |
| Lauralton Hall | | |
| Amity | | |
| Branford | | |
| Shelton | | |
| Wilbur Cross | | |
| Foran | | |
| North Haven | | |
| Sacred Heart Academy | | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Away | Lyman Hall | | | | East Rock Park - East Rock Park | |
| Wilbur Cross | | |
| Foran | | |