| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 10/2 | 3:45 p.m. | Varsity | League | Normal | Away | Morgan | | | | Indian River Complex-XC Course | |
| THU 10/8 | 3:45 p.m. | Varsity | League | Normal | Home | LymeOldLyme | | | | Portland High School-HS Track | |
| THU 10/15 | 3:45 p.m. | Varsity | League | Normal | Away | NathanHaleRay | | | | Nathan Hale Ray High School-Baseball # 1 | |
| THU 10/22 | 3:45 p.m. | Varsity | League | Normal | Home | EastHampton | | | | Portland High School-HS Track | |
| THU 10/29 | 3:30 p.m. | Varsity | League | Normal | Away | ValleyReg | | | | John Winthrop Middle School | |
| FRI 11/6 | 11:30 a.m. | Varsity | League | Normal | Home | CoginchaugReg | | | | TBA-Totoket Park in North Branford | |