| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/31 | 9:30 AM | Varsity | Scrimmage | Normal | Away | Morgan | | | | Old Saybrook High School - Old Saybrook Campus | |
| Old Saybrook | | |
| TUE 9/10 | 3:45 PM | Varsity | League | Normal | Away | Old Lyme | | | | Indian River Complex - XC Course | |
| Old Saybrook | | |
| Morgan | | |
| TUE 9/24 | 3:45 PM | Varsity | League | Normal | Away | Morgan | | | | Cromwell High School - cross country course | |
| North Branford | | |
| Cromwell | | |
| Haddam Killingworth | | |
| THU 10/17 | 1:30 PM | Varsity | Postseason | Normal | Away | Haddam Killingworth | | | | Hammonasset Park | |
| | |
| Coginchaug | | |
| Cromwell | | |
| East Hampton | | |
| East Hampton | | |
| North Branford | | |
| Old Saybrook | | |
| Old Saybrook | | |
| Morgan | | |
| Hale Ray | | |
| Old Lyme | | |
| Portland | | |
| Portland | | |
| Westbrook | | |
| MON 10/28 | 4:00 PM | Varsity | Non-League | Normal | Home | Guilford | | | | John Winthrop Middle School - John Winthrop Middle School | |