| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/12 | 4:00 p.m. | Varsity | League | Normal | Away | Staples | Tied | 1-1 | | Loeffler Field - Staples HS | |
| FRI 9/14 | 4:00 p.m. | Varsity | League | Normal | Home | Ridgefield | Loss | 6-0 | | Stamford High Soccer Field | |
| THU 9/20 | 4:00 p.m. | Varsity | League | Normal | Home | StJoseph | Loss | 5-0 | | Stamford High Soccer Field | |
| FRI 9/21 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Loss | 6-0 | | Fairfield Warde Grass Soccer Field | |
| MON 9/24 | 5:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | Loss | 6-0 | | Taft Field | |
| THU 9/27 | 7:00 p.m. | Varsity | League | Normal | Away | Norwalk | Win | 4-0 | | Testa Field, NHS | |
| SAT 9/29 | 10:00 a.m. | Varsity | League | Normal | Home | Darien | Loss | 6-3 | | Stamford High Soccer Field | |
| TUE 10/2 | 4:00 p.m. | Varsity | League | Normal | Away | BridgeportCentral | Win | 4-0 | | Kennedy Stadium | |
| THU 10/4 | 4:00 p.m. | Varsity | League | Normal | Home | Greenwich | Loss | 6-0 | | Stamford High Soccer Field | |
| SAT 10/6 | 2:00 p.m. | Varsity | League | Normal | Away | Westhill | Loss | 3-0 | | Westhill Front Turf Field | |
| THU 10/11 | 7:00 p.m. | Varsity | League | Normal | Away | BrienMcMahon | Loss | 3-1 | | Brien McMahon HS | |
| MON 10/15 | 4:00 p.m. | Varsity | League | Normal | Home | TrinityCatholic | Win | 6-0 | | Stamford High School | |
| WED 10/17 | 4:00 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 2-0 | | Stamford High Soccer Field | |
| FRI 10/19 | 4:00 p.m. | Varsity | League | Normal | Home | Wilton | Loss | 5-0 | | Stamford High Soccer Field | |
| TUE 10/23 | 4:00 p.m. | Varsity | League | Normal | Home | Trumbull | Loss | 0-6 | | Stamford High Soccer Field | |
| THU 10/25 | 4:00 p.m. | Varsity | League | Normal | Home | Danbury | Loss | 1-5 | | Stamford High Soccer Field | |