| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Away | Jonathan Law | | | | Sheehan High School - Sheehan HS Cross Country Course | 2:30 PM - 1 Bus - Boys and girls travel together |
| North Haven | | |
| Lyman Hall | | |
| Sheehan | | |
| Foran | | |
| North Branford | | |
| Cromwell | | |
| FRI 9/15 | 3:30 PM | Varsity | Non-League | Normal | Away | Middletown | | | | Veterans Memorial Park, Middletown, CT - Veterans Memorial Park, Middletown, CT | |
| Conard | | |
| East Catholic | | |
| Morgan | | |
| Avon | | |
| Naugatuck | | |
| Maloney | | |
| Old Saybrook | | |
| Rocky Hill | | |
| Plainville | | |
| Lewis Mills | | |
| Sacred Heart Academy | | |
| Portland | | |
| Wethersfield | | |
| WED 9/20 | 3:30 PM | Varsity | Non-League | Normal | Home | Nonnewaug | | | | Coginchaug Regional High School - Coginchaug Regional HS | |
| Holy Cross | | |
| Hale Ray | | |
| Maloney | | |
| Housatonic Regional | | |
| Thomaston | | |
| Platt | | |
| East Catholic | | |
| Parish Hill | | |
| Avon | | |
| Old Saybrook | | |
| East Hampton | | |
| New London | | |
| Valley Regional | | |
| Portland | | |
| TUE 10/24 | 3:45 PM | Varsity | League | Normal | Away | Cromwell | | | | Old Saybrook High School - Old Saybrook Campus | |
| Haddam Killingworth | | |
| Old Saybrook | | |
| Valley Regional | | |
| Westbrook | | |
| Portland | | |
| Morgan | | |
| East Hampton | | |
| Hale Ray | | |
| Old Lyme | | |
| North Branford | | |