| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/6 | 4:00 PM | Varsity | League | Normal | Home | | | | | Sheehan High School - Sheehan HS Cross Country Course | |
| TUE 9/10 | 4:00 PM | Varsity | League | Normal | Away | East Haven | | | | Wharton Brook State Park - Wharton Brook State Park | 2:00 PM - 1 Bus |
| Fairfield Prep | | |
| Lyman Hall | | |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | Xavier | | | | Fitzgerald Field - Fitzgerald Field | |
| Amity | | |
| Career Magnet | | |
| SAT 9/21 | 11:00 AM | Varsity | Non-League | Normal | Home | | | | | Winding Trails - Winding Trails-Farmington | |
| TUE 10/8 | 3:30 PM | Varsity | League | Normal | Away | Cheshire | | | | Carrigan Middle School - Baseball Field | |
| Branford | | |
| Notre Dame-West Haven | | |
| FRI 10/18 | 1:30 PM | Varsity | League | Normal | Home | | | | | TBA - TBA | |
| MON 10/21 | 4:00 PM | Varsity | League | Normal | Away | Platt Tech | | | | EISENHOWER PARK - EISENHOWER PARK | 2:30 PM - 1 Bus |
| Foran | | |
| Lauralton Hall | | |
| SAT 10/26 | 3:45 PM | Varsity | League | Normal | Home | | | | | Eisenhower Park - Eisenhower Park | |