| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 10/1 | 4:00 p.m. | Varsity | League | Normal | Away | Stamford | Tied | 0-0 | | Stamford High School-Boyle Stadium | |
| SAT 10/3 | 3:30 p.m. | Varsity | League | Normal | Home | Darien | Loss | 0-10 | | Westhill High School-J. Walter Kennedy Stadium | |
| WED 10/7 | 4:30 p.m. | Varsity | League | Normal | Away | Greenwich | Loss | 0-5 | | Greenwich High School-Cardinal Stadium | |
| FRI 10/9 | 4:00 p.m. | Varsity | League | Normal | Away | NewCanaan | Loss | 0-4 | | New Canaan High School-Dunning Stadium | |
| THU 10/15 | 4:15 p.m. | Varsity | League | Normal | Home | Stamford | | | | Westhill High School-J. Walter Kennedy Stadium | |
| WED 10/21 | 4:00 p.m. | Varsity | League | Normal | Away | Darien | Loss | 0-10 | | Darien High School-DHS Stadium Field | |
| FRI 10/23 | 4:00 p.m. | Varsity | League | Normal | Home | Greenwich | Loss | 0-6 | | Westhill High School-J. Walter Kennedy Stadium | |
| WED 10/28 | 4:15 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 0-5 | | Westhill High School-J. Walter Kennedy Stadium | |
| TUE 11/3 | 3:00 p.m. | Varsity | League | Normal | Home | Stamford | | | | Westhill High School-J. Walter Kennedy Stadium | |
| FRI 11/6 | 3:00 p.m. | Varsity | League | Normal | Home | Darien | Loss | 0-6 | | Westhill High School-J. Walter Kennedy Stadium | |
| SAT 11/7 | 4:00 p.m. | Varsity | League | Normal | Away | Stamford | | | | Stamford High School-Boyle Stadium | |