| 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 | Greenwich | Loss | 0-7 | | Greenwich High School-Cardinal Stadium | |
| MON 10/5 | 3:45 p.m. | Varsity | League | Normal | Home | Greenwich | Loss | 1-7 | | Scalzi Park | |
| WED 10/7 | 3:45 p.m. | Varsity | League | Normal | Home | Darien | Loss | 1-8 | | Scalzi Park | |
| MON 10/12 | 5:30 p.m. | Varsity | League | Normal | Away | Darien | Loss | 0-6 | | Darien High School-DHS Stadium Field | |
| WED 10/14 | 6:30 p.m. | Varsity | League | Normal | Away | NewCanaan | Loss | 0-6 | | New Canaan High School-Dunning Stadium | |
| MON 10/19 | 3:45 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 0-7 | | Scalzi Park | |
| WED 10/21 | 4:00 p.m. | Varsity | League | Normal | Away | Westhill | Loss | 1-8 | | Westhill High School-J. Walter Kennedy Stadium | |
| MON 10/26 | 3:45 p.m. | Varsity | League | Normal | Home | Westhill | Loss | 1-7 | | Scalzi Park | |
| WED 10/28 | 3:45 p.m. | Varsity | League | Normal | Home | Stamford | Loss | 0-6 | | Scalzi Park | |
| MON 11/2 | 3:00 p.m. | Varsity | League | Normal | Away | Stamford | Loss | 0-8 | | Stamford High School-SHS Upper Soccer Field | |