| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 3:45 PM | Varsity | League | Normal | Home | Old Saybrook | | | | Indian River Complex - XC Course | |
| Valley Regional | | |
| Old Lyme | | |
| FRI 9/15 | 3:30 PM | Varsity | Non-League | Normal | Away | Portland | | | | Veterans Memorial Park, Middletown, CT - Veterans Memorial Park, Middletown, CT | 2:30 PM |
| East Catholic | | |
| Avon | | |
| Maloney | | |
| Naugatuck | | |
| Coginchaug | | |
| Old Saybrook | | |
| Rocky Hill | | |
| Wethersfield | | |
| Lewis Mills | | |
| Conard | | |
| Sacred Heart Academy | | |
| Plainville | | |
| Middletown | | |
| WED 9/27 | 3:30 PM | Varsity | League | Normal | Away | Haddam Killingworth | | | | John Winthrop Middle School - John Winthrop Middle School | 2:15 PM |
| North Branford | | |
| Cromwell | | |
| Valley Regional | | |
| East Hampton | | |
| WED 10/4 | 3:30 PM | Varsity | League | Normal | Home | Valley Regional | | | | Peters Complex - Track | |
| WED 10/11 | 3:30 PM | Varsity | League | Normal | Away | East Hampton | | | | East Hampton High School - Cross Country Course | 2:30 PM |
| TUE 10/24 | 3:45 PM | Varsity | League | Normal | Away | Hale Ray | | | | Old Saybrook High School - Old Saybrook Campus | 12:01 AM |
| Valley Regional | | |
| Westbrook | | |
| Old Lyme | | |
| Haddam Killingworth | | |
| Coginchaug | | |
| Cromwell | | |
| East Hampton | | |
| Old Saybrook | | |
| North Branford | | |
| Portland | | |