| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 8/29 | 4:00 PM | Varsity | Scrimmage | Normal | Away | St. Luke's School | Win | 5-3 | | St Lukes School - upper field #1 | 2:30 PM |
| FRI 8/30 | 4:00 PM | Varsity | Scrimmage | Normal | Away | Lauralton Hall | Win | 4-2 | | Lauralton Hall - Turf Field | 2:30 PM |
| TUE 9/3 | 4:00 PM | Varsity | League | Normal | Away | Greenwich | Loss | 0-8 | | Greenwich High School - Cardinal Stadium | 2:30 PM - JV and varsity travel together |
| FRI 9/6 | 4:00 PM | Varsity | League | Normal | Away | Westhill | Win | 4-0 | | Westhill High School - J. Walter Kennedy Stadium | 2:30 PM - JV and varsity travel together |
| SAT 9/14 | 11:30 AM | Varsity | Non-League | Normal | Away | Weston | Tied | 1-1 | | Weston High School - WHS Lower Turf Field | 10:00 AM |
| FRI 9/20 | 4:00 PM | Varsity | League | Normal | Away | Danbury | | | | Danbury High School - Stadium Turf Field | 2:30 PM - JV and varsity travel together |
| FRI 9/27 | 4:00 PM | Varsity | League | Normal | Away | Darien | | | | Darien High School - DHS Stadium Field | 2:30 PM - JV and varsity travel together |
| TUE 10/8 | 5:00 PM | Varsity | League | Normal | Away | Fairfield Ludlowe | | | | Fairfield Ludlowe High School - Taft Field | 3:45 PM |
| TUE 10/15 | 4:30 PM | Varsity | League | Normal | Away | Ridgefield | | | | Ridgefield High School - Tiger Hollow Stadium | 3:00 PM - JV and varsity travel together |
| THU 10/17 | 4:00 PM | Varsity | League | Normal | Away | New Canaan | | | | New Canaan HS - Dunning Stadium | 2:30 PM - JV and varsity travel together |