| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 8/29 | 5:00 PM | Varsity | Scrimmage | Normal | Home | Joel Barlow | | | | Danbury High School - Stadium Turf Field | |
| FRI 9/1 | 5:00 PM | Varsity | Scrimmage | Normal | Home | New Fairfield | | | | Danbury High School - Stadium Turf Field | |
| WED 9/13 | 7:00 PM | Varsity | League | Normal | Away | Fairfield Ludlowe | Loss | 0-3 | | Fairfield Ludlowe High School - Taft Field | 5:15 PM - 1 Bus - STA V only |
| FRI 9/15 | 3:30 PM | Varsity | Non-League | Normal | Home | Naugatuck | Win | 6-1 | | Danbury High School - Grass Soccer Field | |
| MON 9/18 | 4:45 PM | Varsity | League | Normal | Away | Westhill | Win | 3-1 | | Westhill High School - Westhill Front Turf Field | 3:00 PM - 1 Bus - STA V only (JV switched to home game) |
| WED 9/20 | 4:00 PM | Varsity | League | Normal | Home | Brien McMahon | Loss | 1-2 | | Danbury High School - Stadium Turf Field | |
| FRI 9/22 | 4:30 PM | Varsity | League | Normal | Home | Wilton | Loss | 0-4 | | Danbury High School - Stadium Turf Field | |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Away | Stamford | Loss | 1-2 | | West Beach Field - West Beach Field | 2:15 PM - 1 Bus - STA V/JV |
| SAT 9/30 | 10:00 AM | Varsity | League | Normal | Away | Fairfield Warde | Loss | 0-3 | | Fairfield Warde High School - Tetreau/Davis Field | 8:15 AM - 1 Bus - STA V/JV (from 9/29 moved to 9/30) |
| TUE 10/3 | 5:00 PM | Varsity | League | Normal | Home | Greenwich | Loss | 0-2 | | Danbury High School - Stadium Turf Field | |
| THU 10/5 | 4:00 PM | Varsity | League | Normal | Home | Norwalk | Win | 4-0 | | Danbury High School - Stadium Turf Field | |
| SAT 10/7 | 5:00 PM | Varsity | League | Normal | Home | Trumbull | Loss | 0-6 | | Danbury High School - Stadium Turf Field | |
| MON 10/9 | 6:00 PM | Varsity | League | Normal | Home | Ridgefield | Loss | 1-5 | | Danbury High School - Stadium Turf Field | |
| THU 10/12 | 6:00 PM | Varsity | League | Normal | Away | Darien | Loss | 1-6 | | Darien High School - DHS Stadium Field | 4:00 PM - 1 Bus - STA V only |
| MON 10/16 | 4:00 PM | Varsity | League | Normal | Home | Staples | Loss | 2-7 | | Danbury High School - Stadium Turf Field | |
| WED 10/18 | 4:00 PM | Varsity | League | Normal | Away | Bridgeport Central | Win | 4-0 | | Bridgeport Central - Kennedy Stadium Turf | 2:15 PM - 1 Bus - STA V only |
| FRI 10/20 | 4:00 PM | Varsity | League | Normal | Away | New Canaan | Loss | 1-5 | | New Canaan HS - Dunning Stadium | 2:15 PM - 1 Bus - STA V/JV |
| MON 10/23 | 4:30 PM | Varsity | League | Normal | Away | St. Joseph | Loss | 0-7 | | St. Joseph High School - Lower Turf | 2:45 PM - 1 Bus - STA V/JV |