| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/24 | 9:00 AM | Varsity | Scrimmage | Normal | Away | Wilton | Win | 3-2 | | Wilton High School - Lilly Field | 7:30 AM |
| THU 8/29 | 5:15 PM | Varsity | Scrimmage | Normal | Away | Sacred Heart Greenwich | Loss | 1-4 | | Sacred Heart Greenwich - Stadium | 3:30 PM - 84 Passenger Bus |
| MON 9/9 | 4:00 PM | Varsity | League | Normal | Away | Darien | Loss | 0-2 | | Darien High School - DHS Stadium Field | 2:30 PM - JV and Varsity travel together; 84 Passenger Bus |
| SAT 9/14 | 1:00 PM | Varsity | Non-League | Normal | Away | Pomperaug | Win | 4-0 | | Pomperaug High School - Stadium | 8:45 AM - JV and Varsity travel together; 84 Passenger Bus |
| MON 9/16 | 4:30 PM | Varsity | League | Normal | Away | Ridgefield | Win | 3-1 | | Ridgefield High School - Tiger Hollow Stadium | 3:00 PM - JV and Varsity travel together; 84 Passenger Bus |
| MON 9/23 | 5:30 PM | Varsity | League | Normal | Away | Trumbull | | | | Trumbull High School - McDougall Stadium | 4:00 PM - JV and varsity travel together; 84 Passenger Bus |
| WED 9/25 | 5:00 PM | Varsity | League | Normal | Away | Brien McMahon | | | | Brien McMahon High School - Casagrande Field | 3:30 PM - JV and Varsity travel together; 84 Passenger Bus |
| THU 10/10 | 4:00 PM | Varsity | League | Normal | Away | New Canaan | | | | New Canaan HS - Dunning Stadium | 2:30 PM - JV and Varsity travel together; 84 Passenger Bus |
| TUE 10/15 | 4:00 PM | Varsity | League | Normal | Away | Stamford | | | | Stamford High School - Boyle Stadium | 2:30 PM - JV and Varsity travel together; 84 Passenger Bus |
| MON 10/21 | 4:00 PM | Varsity | League | Normal | Away | Staples | | | | Staples High School - Ginny Parker Field | 2:45 PM - JV and Varsity travel together; 84 Passenger |