| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 8/30 | 5:30 PM | Varsity | Scrimmage | Normal | Home | Shelton | | | | Trumbull High School - Cork Field | |
| THU 8/31 | 3:45 PM | Varsity | Scrimmage | Normal | Away | Amity | | | | Amity Regional High School - William Johnson Stadium Field | 2:45 PM - 1 Bus |
| MON 9/4 | 4:30 PM | Varsity | Scrimmage | Normal | Away | Joel Barlow | | | | Joel Barlow High School - Field J (Competition Field) | 3:00 PM - 1 Bus |
| THU 9/7 | 7:00 PM | Varsity | League | Normal | Home | Westhill | Win | 8-0 | | Trumbull High School - Cork Field | |
| WED 9/13 | 5:30 PM | Varsity | League | Normal | Home | Fairfield Warde | Win | 3-1 | | Trumbull High School - Cork Field | |
| MON 9/18 | 5:45 PM | Varsity | League | Normal | Home | Brien McMahon | Tied | 2-2 | | Trumbull High School - Cork Field | |
| WED 9/20 | 6:30 PM | Varsity | League | Normal | Away | Wilton | Win | 1-0 | | Wilton HS - Lilly Field | 4:30 PM - 1 Bus |
| FRI 9/22 | 4:00 PM | Varsity | League | Normal | Away | Bridgeport Central | Win | 7-0 | | Bridgeport Central - Kennedy Stadium Turf | 2:45 PM - 1 Bus |
| WED 9/27 | 5:30 PM | Varsity | League | Normal | Home | Darien | Win | 4-1 | | Trumbull High School - Cork Field | |
| SAT 9/30 | 11:30 AM | Varsity | League | Normal | Home | Greenwich | Tied | 2-2 | | Trumbull High School - Cork Field | |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Away | St. Joseph | Loss | 0-6 | | St. Joseph High School - Lower Turf | 3:00 PM - 1 Bus |
| THU 10/5 | 5:30 PM | Varsity | League | Normal | Home | Stamford | Tied | 0-0 | | Trumbull High School - Cork Field | |
| SAT 10/7 | 5:00 PM | Varsity | League | Normal | Away | Danbury | Win | 6-0 | | Danbury High School - Stadium Turf Field | 2:45 PM - 1 Bus |
| MON 10/9 | 6:00 PM | Varsity | League | Normal | Away | Norwalk | Win | 5-2 | | Norwalk High School - Testa Field | 4:15 PM - 1 Bus |
| THU 10/12 | 5:30 PM | Varsity | League | Normal | Home | Staples | Loss | 1-2 | | Trumbull High School - Cork Field | |
| MON 10/16 | 5:30 PM | Varsity | League | Normal | Home | Ridgefield | Loss | 0-1 | | Trumbull High School - Cork Field | |
| WED 10/18 | 7:00 PM | Varsity | League | Normal | Away | New Canaan | Tied | 1-1 | | New Canaan HS - Dunning Stadium | 5:00 PM - 1 Bus |
| MON 10/23 | 7:00 PM | Varsity | League | Normal | Away | Fairfield Ludlowe | Loss | 0-1 | | Fairfield Ludlowe High School - Taft Field | 5:30 PM - 1 Bus |
| THU 10/26 | 3:30 PM | Varsity | Postseason | Normal | Away | Staples | Loss | 2-4 | | Staples High School - Wakeman Field B (turf) | 1:45 PM - 1 Bus |
| WED 11/1 | 4:00 PM | Varsity | Scrimmage | Normal | Away | | | | | Rye Country Day School | 2:15 PM - 1 Bus |
| MON 11/6 | 2:00 PM | Varsity | Postseason | Normal | Home | Enfield | Win | 1-0 | | Trumbull High School - Cork Field | |
| WED 11/8 | 6:00 PM | Varsity | Postseason | Normal | Away | Norwich Free Academy | Loss | 1-3 | | Norwich Free Academy - Turf Field | 3:15 PM - 1 Bus |