| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 3/20 | 5:00 PM | Varsity | Scrimmage | Normal | Home | | | | | Ridgefield High School - Tiger Hollow Stadium | |
| SAT 3/23 | Canceled | Varsity | League | Canceled | Away | | | | | Staples High School - Ginny Parker Field | |
| | |
| Joel Barlow | | |
| Fairfield Ludlowe | | |
| Greenwich | | |
| Staples | | |
| Cheshire | | |
| St. Joseph | | |
| Newtown | | |
| SUN 3/24 | 8:00 AM | Varsity | Scrimmage | Normal | Away | New Milford | | | | New Milford High School - Joe Wiser Stadium - NMHS | 12:01 AM - 2 Buses - Varsity 12:30PM / JV 2:00PM |
| Brookfield | | |
| Immaculate | | |
| Trumbull | | |
| Bethel | | |
| Fairfield Warde | | |
| Lewis Mills | | |
| New Fairfield | | |
| Danbury | | |
| Stamford | | |
| Westhill | | |
| MON 4/1 | 4:30 PM | Varsity | Scrimmage | Normal | Home | Fairfield Ludlowe | | | | Ridgefield High School - Tiger Hollow Turf Field II | |
| THU 4/4 | 4:00 PM | Varsity | Non-League | Normal | Away | | Loss | 9-20 | | Nyack High School - field | 2:00 PM - 1 Bus |
| SAT 4/6 | 1:00 PM | Varsity | League | Normal | Away | Daniel Hand | Win | 18-4 | | Madison Surf Club - Strong Field | 8:30 AM - 1 Bus - V & JV together; Coach Bus Arrives 8AM |
| TUE 4/9 | 4:00 PM | Varsity | League | Normal | Away | St. Joseph | Win | 14-0 | | St. Joseph High School - Lower Turf | 2:30 PM - 1 Bus |
| THU 4/11 | 4:00 PM | Varsity | League | Normal | Away | New Canaan | Loss | 7-16 | | New Canaan HS - Dunning Stadium | 2:30 PM - 1 Bus |
| SUN 4/14 | 2:00 PM | Varsity | Non-League | Normal | Home | | Win | 11-10 | | Ridgefield High School - Tiger Hollow Stadium | |
| SAT 4/20 | 6:00 PM | Varsity | Non-League | Normal | Away | | Win | 12-11 | | Rye HS - Field | 4:00 PM - 1 Bus |
| TUE 4/23 | 4:30 PM | Varsity | League | Normal | Home | Danbury | Win | 12-1 | | Ridgefield High School - Tiger Hollow Stadium | |
| THU 4/25 | 7:00 PM | Varsity | Non-League | Normal | Away | Newtown | Win | 19-8 | | Newtown High School - Blue and Gold Stadium | 4:45 PM - 1 Bus |
| SAT 4/27 | 12:00 PM | Varsity | Non-League | Normal | Home | New Fairfield | Win | 16-6 | | Ridgefield High School - Tiger Hollow Stadium | |
| MON 4/29 | 5:00 PM | Varsity | League | Normal | Away | Brien McMahon | Win | 19-4 | | Brien McMahon High School - Casagrande Field | 3:15 PM - 1 Bus |
| THU 5/2 | 4:30 PM | Varsity | League | Normal | Home | Greenwich | Win | 12-6 | | Ridgefield High School - Tiger Hollow Stadium | |
| SAT 5/4 | 3:00 PM | Varsity | League | Normal | Home | Wilton | Loss | 10-18 | | Ridgefield High School - Tiger Hollow Stadium | |
| TUE 5/7 | 4:30 PM | Varsity | Non-League | Normal | Home | Amity | Win | 20-10 | | Ridgefield High School - Tiger Hollow Stadium | |
| THU 5/9 | 4:30 PM | Varsity | League | Normal | Away | | Win | 10-6 | | Greenwich Academy - Turf field | 2:20 PM - 1 Bus |
| SAT 5/11 | 1:30 PM | Varsity | League | Normal | Away | Staples | Win | 12-2 | | Staples High School - Ginny Parker Field | 12:00 PM - 1 Bus |
| MON 5/13 | 4:30 PM | Varsity | League | Normal | Home | Darien | Loss | 6-18 | | Ridgefield High School - Tiger Hollow Stadium | |
| THU 5/16 | 5:00 PM | Varsity | Postseason | Normal | Home | Greenwich | Loss | 11-13 | | Ridgefield High School - Tiger Hollow Stadium | |
| TUE 5/28 | 5:00 PM | Varsity | Postseason | Normal | Home | Norwalk | Win | 15-3 | | Ridgefield High School - Tiger Hollow Stadium | |
| SAT 6/1 | 3:00 PM | Varsity | Postseason | Normal | Home | Greenwich | Loss | 8-10 | | Ridgefield High School - Tiger Hollow Stadium | |