| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 10/2 | 4:00 p.m. | Varsity | League | Normal | Away | NewCanaan | | | | New Canaan High School-Dunning Stadium | |
| MON 10/19 | 4:00 p.m. | Varsity | League | Normal | Home | Stamford | | | | Darien High School-DHS Stadium Field | |
| FRI 10/23 | 4:00 p.m. | Varsity | League | Normal | Home | Greenwich | | | | Darien High School-DHS Stadium Field | |
| FRI 10/30 | 4:00 p.m. | Varsity | League | Normal | Home | Westhill | | | | Darien High School-DHS Stadium Field | |