| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/31 | 9:30 AM | Varsity | Scrimmage | Normal | Home | Morgan | | | | Old Saybrook High School - Old Saybrook Campus | |
| Valley Regional | | |
| TUE 9/10 | 3:45 PM | Varsity | League | Normal | Away | Valley Regional | | | | Indian River Complex - XC Course | |
| Morgan | | |
| Old Lyme | | |
| TUE 9/24 | 3:45 PM | Varsity | League | Normal | Away | Coginchaug | | | | Camp Ingersoll - Camp Ingersoll | 2:15 PM |
| Westbrook | | |
| Old Lyme | | |
| Portland | | |
| Hale Ray | | |
| THU 10/10 | 3:30 PM | Varsity | League | Normal | Home | | | | | Old Saybrook High School - Old Saybrook Campus | |
| THU 10/17 | 1:30 PM | Varsity | Postseason | Normal | Away | | | | | Hammonasset Park | |
| | |
| Old Lyme | | |
| Old Lyme | | |
| Morgan | | |
| Morgan | | |
| Hale Ray | | |
| Hale Ray | | |
| Coginchaug | | |
| Coginchaug | | |
| Cromwell | | |
| Cromwell | | |
| East Hampton | | |
| East Hampton | | |
| East Hampton | | |
| East Hampton | | |
| Haddam Killingworth | | |
| Haddam Killingworth | | |
| North Branford | | |
| North Branford | | |
| Portland | | |
| Portland | | |
| Portland | | |
| Portland | | |
| Valley Regional | | |
| Valley Regional | | |
| Westbrook | | |
| Westbrook | | |