| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 8/23 | 1:00 PM | Varsity | Scrimmage | Normal | Away | Branford | | | | Branford High School - Athletic Turf Field | 10:50 AM - 1 Bus - First Student Arrives 10:45 AM |
| TUE 8/27 | 5:15 PM | Varsity | Scrimmage | Normal | Home | Newtown | | | | Ridgefield High School - Tiger Hollow Stadium | |
| THU 8/29 | 5:30 PM | Varsity | Scrimmage | Normal | Away | Conard | | | | Conard High School - McKee Stadium | 3:00 PM - 1 Bus - First Student Arrives 2:45 PM |
| TUE 9/3 | 4:00 PM | Varsity | League | Normal | Away | Staples | Loss | 0-10 | | Staples High School - Ginny Parker Field | 2:30 PM - 1 Bus - First Student Arrives 2:20 PM |
| FRI 9/6 | 6:00 PM | Varsity | League | Normal | Home | Norwalk | Win | 3-2 | | Ridgefield High School - Tiger Hollow Stadium | |
| MON 9/9 | 4:00 PM | Varsity | League | Normal | Away | New Canaan | Win | 2-1 | | New Canaan HS - Dunning Stadium | 2:30 PM - 1 Bus - First Student Arrives 2:20 PM |
| THU 9/12 | 5:00 PM | Varsity | League | Normal | Away | Brien McMahon | Win | 5-0 | | Brien McMahon High School - Casagrande Field | 3:25 PM - 1 Bus - First Student Arrives 3:15 PM |
| SAT 9/14 | 1:00 PM | Varsity | Non-League | Normal | Away | Cheshire | Win | 3-0 | | Cheshire High School - Alumni Field - Turf | 10:45 AM - 1 Bus - LandJet Arrives 10:45 AM |
| MON 9/16 | 4:30 PM | Varsity | League | Normal | Home | Fairfield Ludlowe | Loss | 1-3 | | Ridgefield High School - Tiger Hollow Stadium | |
| THU 9/19 | 5:30 PM | Varsity | League | Normal | Away | Trumbull | | | | Trumbull High School - McDougall Stadium | 3:15 PM - 1 Bus - First Student Arrives 3:00 PM |
| MON 9/23 | 5:00 PM | Varsity | League | Normal | Home | Danbury | | | | Ridgefield High School - Tiger Hollow Stadium | |
| THU 9/26 | 6:30 PM | Varsity | League | Normal | Home | Greenwich | | | | Ridgefield High School - Tiger Hollow Stadium | |
| SAT 9/28 | 10:00 AM | Varsity | League | Normal | Home | Stamford | | | | Ridgefield High School - Tiger Hollow Stadium | |
| WED 10/2 | 4:30 PM | Varsity | Non-League | Normal | Home | New Milford | | | | Ridgefield High School - Tiger Hollow Stadium | |
| MON 10/7 | 4:00 PM | Varsity | League | Normal | Away | St. Joseph | | | | St. Joseph High School - Upper Turf | 2:30 PM - 1 Bus - First Student Arrives 2:20 PM |
| WED 10/9 | 4:30 PM | Varsity | League | Normal | Home | Darien | | | | Ridgefield High School - Tiger Hollow Stadium | |
| TUE 10/15 | 4:30 PM | Varsity | League | Normal | Home | Fairfield Warde | | | | Ridgefield High School - Tiger Hollow Stadium | |
| FRI 10/18 | 6:30 PM | Varsity | League | Normal | Away | Wilton | | | | Wilton HS - Fuijitani Field -Turf | 5:00 PM - 1 Bus - First Student Arrives 4:50 PM |
| TUE 10/22 | 4:00 PM | Varsity | League | Normal | Away | Westhill | | | | Westhill High School - J. Walter Kennedy Stadium | 2:30 PM - 1 Bus - First Student Arrives 2:20 PM |
| THU 10/24 | 12:01 AM | Varsity | Postseason | Normal | Home | | | | | Ridgefield High School - Tiger Hollow Stadium | |