| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 8/30 | 6:00 PM | Varsity | Scrimmage | Normal | Home | New Milford | | | | Stamford High School - SHS Upper Soccer Field | |
| SAT 9/9 | 10:30 AM | Varsity | Non-League | Normal | Away | Harding | Win | 10-0 | | Warren Harding High School - Lewis Field | 8:45 AM |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Home | Brien McMahon | Loss | 1-2 | | Stamford High School - SHS Upper Soccer Field | |
| WED 9/13 | 4:30 PM | Varsity | League | Normal | Home | Bridgeport Central | Win | 8-0 | | Stamford High School - SHS Upper Soccer Field | |
| MON 9/18 | 4:00 PM | Varsity | League | Normal | Away | Darien | Loss | 0-4 | | Darien High School - [CIAC] Willow Brook Park | 2:45 PM |
| WED 9/20 | 4:30 PM | Varsity | League | Normal | Away | Staples | Loss | 1-5 | | Staples High School - Wakeman Field B (turf) | 2:30 PM |
| FRI 9/22 | 5:00 PM | Varsity | League | Normal | Away | Ridgefield | Loss | 0-4 | | Ridgefield High School - Tiger Hollow Stadium | |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Home | Danbury | Win | 2-1 | | West Beach Field - West Beach Field | |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Away | Westhill | Win | 3-1 | | Westhill High School - J. Walter Kennedy Stadium | 2:45 AM |
| THU 10/5 | 5:30 PM | Varsity | League | Normal | Away | Trumbull | Tied | 0-0 | | Trumbull High School - Cork Field | 3:15 PM |
| SAT 10/7 | 1:00 PM | Varsity | League | Normal | Away | New Canaan | Loss | 0-3 | | New Canaan HS - Dunning Stadium | 11:30 AM |
| MON 10/9 | 4:30 PM | Varsity | League | Normal | Away | Greenwich | Loss | 0-1 | | Greenwich High School - Field 3 | 3:15 PM |
| THU 10/12 | 7:00 PM | Varsity | League | Normal | Away | Fairfield Ludlowe | Loss | 0-5 | | Fairfield Ludlowe High School - Taft Field | 4:30 PM |
| MON 10/16 | 6:30 PM | Varsity | League | Normal | Away | Fairfield Warde | Loss | 1-2 | | Fairfield Warde High School - Tetreau/Davis Field | 4:30 PM |
| WED 10/18 | 4:15 PM | Varsity | League | Normal | Home | Norwalk | Win | 3-0 | | West Beach Field - West Beach Field | |
| FRI 10/20 | 4:30 PM | Varsity | League | Normal | Away | St. Joseph | Loss | 0-5 | | St. Joseph High School - Lower Turf | 2:15 PM |
| MON 10/23 | 4:00 PM | Varsity | League | Normal | Home | Wilton | Win | 2-1 | | West Beach Field - West Beach Field | |
| MON 11/6 | 6:00 PM | Varsity | Tournament | Normal | Away | Cheshire | Loss | 0-5 | | Cheshire High Main Game field - Cheshire High Main Game field | 2:45 PM |