| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Away | Coginchaug | | | | Sheehan High School - Sheehan HS Cross Country Course | 2:15 PM |
| Cromwell | | |
| Jonathan Law | | |
| Foran | | |
| Lyman Hall | | |
| North Haven | | |
| Sheehan | | |
| WED 9/27 | 3:30 PM | Varsity | League | Normal | Away | Cromwell | | | | John Winthrop Middle School - John Winthrop Middle School | 2:15 PM |
| East Hampton | | |
| Haddam Killingworth | | |
| Morgan | | |
| Valley Regional | | |
| MON 10/2 | 3:45 PM | Varsity | Non-League | Normal | Away | Lauralton Hall | | | | Eisenhower Park - Eisenhower Park | |
| Amity | | |
| Branford | | |
| Jonathan Law | | |
| Foran | | |
| North Haven | | |
| Sacred Heart Academy | | |
| West Haven | | |
| Wilbur Cross | | |
| TUE 10/24 | 3:45 PM | Varsity | League | Normal | Away | Coginchaug | | | | Old Saybrook High School - Old Saybrook Campus | |
| Cromwell | | |
| East Hampton | | |
| Haddam Killingworth | | |
| Old Lyme | | |
| Morgan | | |
| Hale Ray | | |
| Old Saybrook | | |
| Portland | | |
| Valley Regional | | |
| Westbrook | | |