| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 10/1 | 3:45 p.m. | Varsity | League | Normal | Home | Cromwell | | | | John Winthrop Middle School | |
| THU 10/8 | 4:15 p.m. | Varsity | League | Normal | Home | Morgan | | | | John Winthrop Middle School | |
| THU 10/15 | 3:30 p.m. | Varsity | League | Normal | Away | NorthBranford | | | | Totoket Valley Park - North Branford-Totoket Park - North Branford | |
| TUE 10/20 | 3:45 p.m. | Varsity | League | Normal | Away | HaddamKillingworth | | | | Haddam Killingworth High School (HK)-HKHS Cross Country Course | |
| TUE 10/27 | 3:30 p.m. | Varsity | League | Normal | Home | Portland | | | | John Winthrop Middle School | |
| THU 11/5 | 2:30 p.m. | Varsity | League | Normal | Home | LymeOldLyme | | | | Totoket Valley Park-Cross Country Course | |