| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 8/29 | 4:00 PM | Varsity | Scrimmage | Normal | Away | | | | | Lakeland HS - Stadium Turf | 2:20 PM - 1 Bus - Arrive 2:20; Depart 2:30 |
| THU 8/31 | 4:00 PM | Varsity | Scrimmage | Normal | Home | | | | | Ridgefield High School - Tiger Hollow Stadium | |
| SAT 9/2 | 9:00 AM | Varsity | Scrimmage | Normal | Away | Newtown | | | | New Fairfield High School - Marty Morgan Field | 8:00 AM - 1 Bus - Arrive 8:00; Depart 8:15 |
| Weston | | |
| Brookfield | | |
| Amity | | |
| Bethel | | |
| Masuk | | |
| New Fairfield | | |
| New Milford | | |
| Shepaug Valley | | |
| TUE 9/5 | Canceled | Varsity | Scrimmage | Canceled | Away | | | | | Kent School - Turf Field | |
| THU 9/7 | 7:30 PM | Varsity | League | Normal | Home | New Canaan | Win | 4-2 | | Ridgefield High School - Tiger Hollow Stadium | |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Home | Brien McMahon | Win | 6-2 | | Ridgefield High School - Tiger Hollow Stadium | |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Away | Fairfield Ludlowe | Win | 7-1 | | Fairfield Ludlowe High School - Taft Field | 1:45 PM - 1 Bus - Arrive 1:45; Depart 2:00 |
| TUE 9/19 | 4:00 PM | Varsity | League | Normal | Home | Trumbull | Win | 4-0 | | Ridgefield High School - Tiger Hollow Stadium | |
| SAT 9/23 | 9:45 AM | Varsity | League | Normal | Away | Danbury | Win | 8-0 | | Danbury High School - Stadium Turf Field | 8:30 AM - 1 Bus - Arrive 8:30; 8:40 |
| WED 9/27 | 6:00 PM | Varsity | League | Normal | Away | Greenwich | Win | 2-1 | | Greenwich High School - Cardinal Stadium | 3:30 PM - 1 Bus - Arrive 3:30; Depart 3:45 |
| SAT 9/30 | 4:00 PM | Varsity | League | Normal | Away | Stamford | Win | 4-0 | | Stamford High School - Boyle Stadium | 2:00 PM - 1 Bus |
| THU 10/5 | 4:00 PM | Varsity | League | Normal | Home | St. Joseph | Win | 9-0 | | Ridgefield High School - Tiger Hollow Stadium | |
| FRI 10/6 | 5:30 PM | Varsity | Non-League | Normal | Away | New Milford | Win | 3-0 | | New Milford High School - Joe Wiser Stadium - NMHS | 3:45 PM - 1 Bus - Arrive 3:45; Depart 3:55 |
| MON 10/9 | 4:00 PM | Varsity | League | Normal | Away | Darien | Loss | 1-4 | | Darien High School - DHS Stadium Field | 2:15 PM - 1 Bus - Arrive 2:15; Depart 2:25 |
| WED 10/11 | 4:00 PM | Varsity | League | Normal | Away | Fairfield Warde | Win | 6-0 | | Fairfield Warde High School - Tetreau/Davis Field | 2:00 PM - 1 Bus - Arrive 2:00; Depart 2:15 |
| FRI 10/13 | 5:00 PM | Varsity | League | Normal | Home | Wilton | Loss | 2-3 | | Ridgefield High School - Tiger Hollow Stadium | |
| MON 10/16 | 6:30 PM | Varsity | League | Normal | Home | Westhill | Win | 6-0 | | Ridgefield High School - Tiger Hollow Stadium | |
| FRI 10/20 | 6:30 PM | Varsity | League | Normal | Away | Norwalk | Win | 2-1 | | Norwalk High School - Testa Field | 4:45 PM - 1 Bus - Arrive 4:45; Depart 4:55 |
| TUE 10/24 | 5:00 PM | Varsity | League | Normal | Home | Staples | Loss | 1-2 | | Ridgefield High School - Tiger Hollow Stadium | |
| FRI 10/27 | 3:30 PM | Varsity | Postseason | Normal | Home | Norwalk | | | | Ridgefield High School - Tiger Hollow Stadium | |
| MON 10/30 | Canceled | Varsity | Postseason | Canceled | Away | Staples | | | | Brien McMahon High School - Casagrande Field | |
| WED 11/1 | 7:00 PM | Varsity | Postseason | Normal | Away | Staples | Loss | 2-3 | | Brien McMahon High School - Casagrande Field | 5:00 PM - 1 Bus |
| WED 11/8 | 4:00 PM | Varsity | Postseason | Normal | Home | Enfield | Win | 4-1 | | Ridgefield High School - Tiger Hollow Stadium | |
| FRI 11/10 | 3:00 PM | Varsity | Postseason | Normal | Home | Wilton | Loss | 0-1 | | Ridgefield High School - Tiger Hollow Stadium | |