| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 9/2 | 10:00 AM | Varsity | Scrimmage | Normal | Away | Norwalk | | | | Norwalk High School - Testa Field | 9:00 AM |
| TUE 9/5 | 4:45 PM | Varsity | League | Normal | Away | | | | | St Lukes School - upper field #1 | 2:15 PM |
| THU 9/7 | 6:45 PM | Varsity | League | Normal | Away | Wilton | Loss | 0-7 | | Wilton HS - Fuijitani Field -Turf | 3:30 PM - JV and varsity travel together |
| MON 9/11 | 4:15 PM | Varsity | Non-League | Normal | Home | Weston | Loss | 1-3 | | Fairfield Warde High School - Tetreau/Davis Field | |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Away | Stamford | Loss | 0-1 | | Stamford High School - Boyle Stadium | 2:30 PM - JV and Varsity travel together |
| MON 9/18 | 4:00 PM | Varsity | League | Normal | Home | Danbury | Loss | 1-2 | | Fairfield Warde High School - Tetreau/Davis Field | |
| THU 9/21 | 4:00 PM | Varsity | League | Normal | Away | Staples | Loss | 0-10 | | Staples High School - Ginny Parker Field | 2:30 PM - JV and Varsity travel together |
| TUE 9/26 | 7:00 PM | Varsity | League | Normal | Away | Trumbull | Loss | 1-4 | | Trumbull High School - McDougall Stadium | 4:15 PM - JV and Varsity travel together |
| THU 9/28 | 4:00 PM | Varsity | League | Normal | Home | Darien | Loss | 0-10 | | Fairfield Warde High School - Tetreau/Davis Field | |
| TUE 10/3 | 5:00 PM | Varsity | League | Normal | Away | Brien McMahon | Loss | 0-1 | | Brien McMahon High School - Casagrande Field | 3:30 PM - JV and Varsity travel together |
| WED 10/4 | 4:00 PM | Varsity | League | Normal | Home | New Canaan | Loss | 1-5 | | Fairfield Warde High School - Tetreau/Davis Field | |
| FRI 10/6 | 4:00 PM | Varsity | League | Normal | Home | Fairfield Ludlowe | Loss | 0-5 | | Fairfield Warde High School - Tetreau/Davis Field | |
| MON 10/9 | 4:00 PM | Varsity | League | Normal | Away | St. Joseph | Loss | 2-3 | | St. Joseph High School - Upper Turf | 2:30 PM - JV and Varsity travel together |
| WED 10/11 | 4:00 PM | Varsity | League | Normal | Home | Ridgefield | Loss | 0-6 | | Fairfield Warde High School - Tetreau/Davis Field | |
| MON 10/16 | 4:00 PM | Varsity | Non-League | Normal | Away | Amity | Loss | 0-3 | | Amity Regional High School - William Johnson Stadium Field | 2:30 PM - JV and Varsity travel together |
| TUE 10/17 | 6:30 PM | Varsity | League | Normal | Away | Norwalk | Loss | 0-3 | | Norwalk High School - Testa Field | 3:30 PM - JV and Varsity travel together |
| FRI 10/20 | 5:15 PM | Varsity | League | Normal | Home | Westhill | Tied | 2-2 | | Fairfield Warde High School - Tetreau/Davis Field | |
| TUE 10/24 | 4:00 PM | Varsity | League | Normal | Home | Greenwich | Loss | 0-6 | | Fairfield Warde High School - Tetreau/Davis Field | |