| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 10/1 | 3:45 p.m. | Varsity | League | Normal | Away | Morgan | | | | Indian River Complex-XC Course | |
| TUE 10/6 | 3:45 p.m. | Varsity | League | Normal | Home | LymeOldLyme | | | | Portland High School-HS Track | |
| WED 10/14 | 3:45 p.m. | Varsity | League | Normal | Away | NathanHaleRay | | | | Nathan Hale Ray High School-Baseball # 1 | |
| TUE 10/20 | 3:45 p.m. | Varsity | League | Normal | Home | EastHampton | | | | Portland High School-HS Track | |
| TUE 10/27 | 3:30 p.m. | Varsity | League | Normal | Away | ValleyReg | | | | John Winthrop Middle School | |
| FRI 11/6 | 11:00 a.m. | Varsity | League | Normal | Home | CoginchaugReg | | | | Coginchaug-Totoket Park in North Branford | |