| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/9 | 2:00 p.m. | Varsity | League | Normal | Away | Norwalk | Loss | 2-5 | | Testa Field, NHS | |
| THU 9/11 | 4:00 p.m. | Varsity | League | Normal | Home | FairfieldWarde | Loss | 4-5 | | | |
| THU 9/18 | 4:00 p.m. | Varsity | League | Normal | Away | Staples | Loss | 2-4 | | Loeffler Field - Staples HS | |
| MON 9/22 | 4:00 p.m. | Varsity | League | Normal | Home | WarrenHarding | Win | 7-3 | | | |
| WED 9/24 | 4:00 p.m. | Varsity | League | Normal | Away | BrienMcMahon | Tied | 1-1 | | Brien McMahon HS | |
| FRI 9/26 | 4:00 p.m. | Varsity | League | Normal | Home | TrinityCatholic | Win | 7-2 | | | |
| TUE 9/30 | 4:00 p.m. | Varsity | League | Normal | Away | BridgeportCentral | Loss | 2-3 | | Kennedy Stadium | |
| THU 10/2 | 4:00 p.m. | Varsity | League | Normal | Away | Stamford | Loss | 0-8 | | Stamford High Soccer Field | |
| MON 10/6 | 4:30 p.m. | Varsity | League | Normal | Home | Wilton | Win | 3-2 | | | |
| WED 10/8 | 4:00 p.m. | Varsity | League | Normal | Away | Westhill | Loss | 2-4 | | Westhill Front Turf Field | |
| FRI 10/10 | 4:00 p.m. | Varsity | League | Normal | Home | Darien | Loss | 1-3 | | | |
| MON 10/13 | 4:00 p.m. | Varsity | League | Normal | Home | StJoseph | Loss | 2-6 | | | |
| WED 10/15 | 4:00 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 1-4 | | | |
| FRI 10/17 | 5:00 p.m. | Varsity | League | Normal | Away | Danbury | Loss | 1-5 | | Danbury High School Stadium | |
| TUE 10/21 | 4:30 p.m. | Varsity | League | Normal | Away | Greenwich | Loss | 0-8 | | Cardinal Stadium | |
| WED 10/22 | 4:00 p.m. | Varsity | League | Normal | Home | FairfieldLudlowe | Loss | 0-3 | | | |