| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 8/30 | 4:00 PM | Varsity | Scrimmage | Normal | Home | Avon | | | | Cromwell High School - cross country course | |
| Berlin | | |
| Granby Memorial | | |
| Hale Ray | | |
| SAT 9/14 | 8:30 AM | Varsity | League | Normal | Home | Haddam Killingworth | | | | Cromwell High School - cross country course | |
| Daniel Hand | | |
| TUE 9/24 | 3:45 PM | Varsity | League | Normal | Home | Haddam Killingworth | | | | Cromwell High School - cross country course | |
| North Branford | | |
| Morgan | | |
| Valley Regional | | |
| THU 10/17 | 1:30 PM | Varsity | Postseason | Normal | Away | Valley Regional | | | | Hammonasset Park | |
| Westbrook | | |
| Morgan | | |
| Hale Ray | | |
| North Branford | | |
| Old Saybrook | | |
| Old Saybrook | | |
| Portland | | |
| Portland | | |
| Haddam Killingworth | | |
| Old Lyme | | |
| East Hampton | | |
| East Hampton | | |
| Coginchaug | | |
| | |