| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 8/29 | 4:00 PM | Varsity | Scrimmage | Normal | Home | Notre Dame-Fairfield | | | | Brien McMahon High School - Pride Field | |
| THU 8/31 | 4:00 PM | Varsity | Scrimmage | Normal | Away | | | | | St. Lukes - Class of 2015 Field | |
| SAT 9/2 | 9:00 AM | Varsity | Tournament | Normal | Home | Not Listed | | | | Brien McMahon High School - Pride Field | |
| SAT 9/2 | 12:20 PM | Varsity | Tournament | Normal | Away | Bunnell | | | | Brien McMahon High School - Pride Field | |
| THU 9/7 | 6:15 PM | Varsity | League | Normal | Home | Greenwich | Loss | 0-2 | | Brien McMahon High School - Pride Field | |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Away | Stamford | Win | 2-1 | | Stamford High School - SHS Upper Soccer Field | |
| WED 9/13 | 4:15 PM | Varsity | League | Normal | Home | Staples | Loss | 0-1 | | Brien McMahon High School - Pride Field | |
| MON 9/18 | 5:45 PM | Varsity | League | Normal | Away | Trumbull | Tied | 2-2 | | Trumbull High School - Cork Field | |
| WED 9/20 | 4:00 PM | Varsity | League | Normal | Away | Danbury | Win | 2-1 | | Danbury High School - Stadium Turf Field | |
| SAT 9/23 | 9:30 AM | Varsity | League | Normal | Home | Fairfield Ludlowe | Loss | 1-3 | | Brien McMahon High School - Pride Field | |
| WED 9/27 | 7:00 PM | Varsity | League | Normal | Home | Westhill | Win | 6-0 | | Brien McMahon High School - Pride Field | |
| SAT 9/30 | 10:00 AM | Varsity | League | Normal | Away | Ridgefield | Tied | 0-0 | | Ridgefield High School - Tiger Hollow Stadium | |
| TUE 10/3 | 7:00 PM | Varsity | League | Normal | Away | Norwalk | Win | 3-0 | | Norwalk High School - Testa Field | |
| THU 10/5 | 4:15 PM | Varsity | League | Normal | Home | New Canaan | Loss | 1-2 | | Brien McMahon High School - Pride Field | |
| SAT 10/7 | 10:00 AM | Varsity | Non-League | Normal | Away | New Fairfield | Win | 2-0 | | New Fairfield High School - Stadium Field | |
| MON 10/9 | 4:00 PM | Varsity | League | Normal | Away | Bridgeport Central | Win | 6-0 | | Bridgeport Central - Kennedy Stadium Turf | |
| THU 10/12 | 4:00 PM | Varsity | League | Normal | Away | St. Joseph | Loss | 1-3 | | St. Joseph High School - Lower Turf | |
| MON 10/16 | 6:30 PM | Varsity | League | Normal | Away | Wilton | Win | 1-0 | | Wilton HS - Lilly Field | |
| WED 10/18 | 4:00 PM | Varsity | League | Normal | Home | Fairfield Warde | Win | 2-1 | | Brien McMahon High School - Pride Field | |
| MON 10/23 | 6:15 PM | Varsity | League | Normal | Home | Darien | Tied | 1-1 | | Brien McMahon High School - Pride Field | |
| WED 11/1 | Canceled | Varsity | Scrimmage | Canceled | Home | Joel Barlow | | | | Brien McMahon High School - Casagrande Field | |
| THU 11/2 | Canceled | Varsity | Scrimmage | Canceled | Away | New Canaan | | | | New Canaan HS - WTT #1 | 12:00 PM |
| MON 11/6 | 4:00 PM | Varsity | Postseason | Normal | Home | Hall | Loss | 1-2 | | Brien McMahon High School - Casagrande Field | |