| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 8/29 | 4:30 PM | Varsity | Scrimmage | Normal | Away | Woodland | | | | Woodland High School - Woodland Soccer Field | 2:45 PM - 1 Bus |
| THU 8/31 | 4:15 PM | Varsity | Scrimmage | Normal | Home | Westhill | | | | Jonathan Law High School - Lawmen Stadium | |
| TUE 9/5 | Canceled | Varsity | Scrimmage | Canceled | Away | Holy Cross | | | | Holy Cross - Alumni Field | 2:15 PM - 1 Bus |
| SAT 9/9 | 9:00 AM | Varsity | Non-League | Normal | Away | Lauralton Hall | Win | 6-0 | | Lauralton Hall - Soccer Field | 2:30 PM - 1 Bus |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Away | North Haven | Win | 3-2 | | North Haven Middle School - West Turf Field | 2:30 PM |
| THU 9/14 | 6:00 PM | Varsity | League | Normal | Home | Daniel Hand | Loss | 0-1 | | Jonathan Law High School - Lawmen Stadium | |
| WED 9/20 | 6:00 PM | Varsity | League | Normal | Home | Amity | Loss | 0-5 | | Jonathan Law High School - Lawmen Stadium | |
| SAT 9/23 | 10:30 AM | Varsity | League | Normal | Away | Shelton | Tied | 1-1 | | Shelton High School - Finn Stadium | 8:00 AM - 1 Bus |
| TUE 9/26 | 6:00 PM | Varsity | League | Normal | Away | East Haven | Win | 6-0 | | East Haven High School - EHHS Turf Field & Track | 4:45 PM - 1 Bus |
| THU 9/28 | 5:00 PM | Varsity | League | Normal | Away | Hamden | Win | 6-1 | | Hamden High School - HHS Turf #2 | 3:30 PM - 1 Bus |
| MON 10/2 | 7:30 PM | Varsity | League | Normal | Home | Foran | Win | 4-1 | | Jonathan Law High School - Lawmen Stadium | |
| WED 10/4 | 6:00 PM | Varsity | League | Normal | Home | Lauralton Hall | Win | 1-0 | | Jonathan Law High School - Lawmen Stadium | |
| SAT 10/7 | 6:00 PM | Varsity | League | Normal | Home | North Haven | Win | 1-0 | | Jonathan Law High School - Lawmen Stadium | |
| TUE 10/10 | 6:00 PM | Varsity | League | Normal | Away | Daniel Hand | Tied | 1-1 | | Madison Surf Club - Surf Club | 4:30 PM - 1 Bus |
| THU 10/12 | 3:45 PM | Varsity | League | Normal | Away | Amity | Loss | 1-3 | | Amity Regional High School - AHS Grass Field # 3 | 2:30 PM - 1 Bus |
| THU 10/19 | 3:45 PM | Varsity | League | Normal | Home | Shelton | Win | 3-2 | | Jonathan Law High School - Lawmen Stadium | |
| FRI 10/20 | 6:00 PM | Varsity | League | Normal | Home | East Haven | Win | 4-0 | | Jonathan Law High School - Lawmen Stadium | |
| MON 10/23 | 6:00 PM | Varsity | League | Normal | Home | Hamden | Win | 5-2 | | Jonathan Law High School - Lawmen Stadium | |
| WED 10/25 | 7:00 PM | Varsity | League | Normal | Away | Foran | Win | 4-3 | | Foran High School - Foran High School - Turf Field | 5:30 PM - 1 Bus |
| SAT 10/28 | 12:00 PM | Varsity | Postseason | Normal | Away | Sacred Heart Academy | Loss | 1-3 | | Sacred Heart Academy - Soccer Field | |
| MON 11/6 | 4:00 PM | Varsity | Postseason | Normal | Home | Farmington | Loss | 1-3 | | Jonathan Law High School - Lawmen Stadium | |