| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 8/22 | 10:30 AM | Varsity | Scrimmage | Normal | Away | Westhill | | | | Westhill High School - Front Turf | 9:00 AM - 1 Bus |
| SAT 8/24 | 8:00 AM | Varsity | League | Normal | Home | Watertown | | | | Jonathan Law High School - Lawmen Stadium | |
| Stamford | | |
| Stratford | | |
| Holy Cross | | |
| Foran | | |
| New Fairfield | | |
| Oxford | | |
| TUE 8/27 | 4:00 PM | Varsity | Scrimmage | Normal | Away | Danbury | | | | New Fairfield High School - Marty Morgan Field | 1:30 PM - 1 Bus |
| Thomaston | | |
| New Fairfield | | |
| THU 8/29 | 3:45 PM | Varsity | Scrimmage | Normal | Away | Woodland | | | | Woodland High School - Woodland Soccer Field | 2:00 PM - 1 Bus |
| TUE 9/3 | 7:00 PM | Varsity | League | Normal | Away | Foran | Win | 4-0 | | Foran High School - Foran High School - Turf Field | 5:00 PM - 1 Bus |
| THU 9/5 | 4:30 PM | Varsity | League | Normal | Home | Branford | Win | 3-0 | | Jonathan Law High School - Lawmen Stadium | |
| TUE 9/10 | 6:00 PM | Varsity | League | Normal | Home | West Haven | Win | 5-2 | | Jonathan Law High School - Lawmen Stadium | |
| THU 9/12 | 4:30 PM | Varsity | League | Normal | Home | Shelton | Win | 4-1 | | Jonathan Law High School - Lawmen Stadium | |
| TUE 9/17 | 6:00 PM | Varsity | League | Normal | Away | Cheshire | Win | 2-1 | | Cheshire High School - Alumni Field - Turf | 3:30 PM - 1 Bus |
| THU 9/19 | 4:30 PM | Varsity | League | Normal | Home | Amity | | | | Jonathan Law High School - Lawmen Stadium | |
| MON 9/23 | 6:00 PM | Varsity | League | Normal | Home | Lauralton Hall | | | | Jonathan Law High School - Lawmen Stadium | |
| WED 9/25 | 6:00 PM | Varsity | League | Normal | Home | East Haven | | | | Jonathan Law High School - Lawmen Stadium | |
| TUE 10/1 | 6:30 PM | Varsity | League | Normal | Away | Branford | | | | Branford High School - Athletic Turf Field | 4:15 PM - 1 Bus |
| FRI 10/4 | 5:30 PM | Varsity | League | Normal | Away | West Haven | | | | West Haven High School - Ken Strong Stadium | 2:15 PM - 1 Bus |
| MON 10/7 | 7:30 PM | Varsity | League | Normal | Away | Shelton | | | | Shelton High School - Finn Stadium | 3:45 PM - 1 Bus |
| WED 10/9 | 6:00 PM | Varsity | League | Normal | Home | Cheshire | | | | Jonathan Law High School - Lawmen Stadium | |
| THU 10/10 | 4:00 PM | Varsity | League | Normal | Away | Amity | | | | Amity Regional High School - William Johnson Stadium Field | 2:15 PM - 1 Bus |
| TUE 10/15 | 3:45 PM | Varsity | League | Normal | Away | Lauralton Hall | | | | Lauralton Hall - Soccer Field | 2:30 PM - 1 Bus |
| FRI 10/18 | 4:15 PM | Varsity | League | Normal | Away | East Haven | | | | East Haven High School - EHHS Turf Field & Track | 9:00 AM - 1 Bus |
| TUE 10/22 | 5:00 PM | Varsity | League | Normal | Home | Foran | | | | Jonathan Law High School - Lawmen Stadium | |