| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 8/29 | 4:00 PM | Varsity | Scrimmage | Normal | Away | Brookfield | | | | Cadigan Field - Cadigan - East | 2:30 PM - 1 Bus - Arrive 2:30; Depart 2:45 |
| THU 8/31 | 5:00 PM | Varsity | Scrimmage | Normal | Away | Joel Barlow | | | | Joel Barlow High School - Field I (Stadium) | 3:30 PM - 1 Bus - Arrive 3:30; Depart 3:35 |
| SAT 9/2 | 10:00 AM | Varsity | Scrimmage | Normal | Home | Weston | | | | Ridgefield High School - Tiger Hollow Stadium | |
| MON 9/4 | 10:00 AM | Varsity | Scrimmage | Normal | Home | Bethel | | | | Ridgefield High School - Tiger Hollow Stadium | |
| MON 9/11 | 4:00 PM | Varsity | League | Normal | Away | Bridgeport Central | Win | 8-0 | | Bridgeport Central - Kennedy Stadium Turf | 2:00 PM - 1 Bus - Arrive 2:00; Depart 2:15 |
| WED 9/13 | 4:00 PM | Varsity | League | Normal | Home | Westhill | Win | 6-0 | | Ridgefield High School - Tiger Hollow Stadium | |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Home | Staples | Tied | 0-0 | | Ridgefield High School - Tiger Hollow Stadium | |
| WED 9/20 | 7:00 PM | Varsity | League | Normal | Away | Norwalk | Win | 4-0 | | Norwalk High School - Testa Field | 5:15 PM - 1 Bus - Arrive 5:15; Depart 5:25 |
| FRI 9/22 | 5:00 PM | Varsity | League | Normal | Home | Stamford | Win | 4-0 | | Ridgefield High School - Tiger Hollow Stadium | |
| SUN 9/24 | 4:30 PM | Varsity | Non-League | Normal | Away | Notre Dame-Fairfield | Tied | 0-0 | | Notre Dame - Fairfield - Park Ave Field | 2:15 PM - 1 Bus - Arrive 2:15; Depart 2:30 |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Home | Fairfield Warde | Tied | 0-0 | | Ridgefield High School - Tiger Hollow Stadium | |
| SAT 9/30 | 10:00 AM | Varsity | League | Normal | Home | Brien McMahon | Tied | 0-0 | | Ridgefield High School - Tiger Hollow Stadium | |
| TUE 10/3 | 6:30 PM | Varsity | League | Normal | Away | Wilton | Win | 1-0 | | Wilton HS - Lilly Field | 4:45 PM - 1 Bus - Arrive 4:45; Depart 5:00 |
| THU 10/5 | 7:00 PM | Varsity | League | Normal | Away | Fairfield Ludlowe | Loss | 1-3 | | Fairfield Ludlowe High School - Taft Field | 4:25 PM - 1 Bus - Arrive 4:20; Depart 4:25 |
| MON 10/9 | 6:00 PM | Varsity | League | Normal | Away | Danbury | Win | 5-1 | | Danbury High School - Stadium Turf Field | 4:30 PM - 1 Bus - Arrive 4:30; Depart 4:45 |
| TUE 10/10 | 4:00 PM | Varsity | League | Normal | Away | St. Joseph | Loss | 2-5 | | St. Joseph High School - Lower Turf | 1:50 PM - 1 Bus - Arrive 1:50; Depart 2:00 |
| THU 10/12 | 6:00 PM | Varsity | League | Normal | Home | Greenwich | Tied | 0-0 | | Ridgefield High School - Tiger Hollow Stadium | |
| MON 10/16 | 5:30 PM | Varsity | League | Normal | Away | Trumbull | Win | 1-0 | | Trumbull High School - Cork Field | 3:15 PM - 1 Bus - Arrive 3:15; Depart 3:30 |
| WED 10/18 | 7:00 PM | Varsity | League | Normal | Home | Darien | Win | 2-1 | | Ridgefield High School - Tiger Hollow Stadium | |
| MON 10/23 | 4:00 PM | Varsity | League | Normal | Home | New Canaan | Tied | 1-1 | | Ridgefield High School - Tiger Hollow Stadium | |
| THU 10/26 | 4:30 PM | Varsity | Postseason | Normal | Away | Fairfield Ludlowe | Win | 1-0 | | Fairfield Ludlowe High School - Taft Field | 2:00 PM - 1 Bus - Arrive 2:00; Depart 2:05 |
| WED 11/1 | 5:00 PM | Varsity | Postseason | Normal | Away | St. Joseph | Loss | 0-4 | | New Canaan HS - Dunning Stadium | 3:00 PM - 1 Bus |
| MON 11/6 | 6:00 PM | Varsity | Postseason | Normal | Home | Wilton | Win | 1-0 | | Ridgefield High School - Tiger Hollow Stadium | |
| WED 11/8 | 6:00 PM | Varsity | Tournament | Normal | Away | Cheshire | Win | 1-0 | | Cheshire High Main Game field - Cheshire High Main Game field | 3:00 PM - 1 Bus - Arrive 3:00; Depart 3:15 |
| FRI 11/10 | 2:00 PM | Varsity | Postseason | Normal | Away | St. Joseph | Loss | 0-3 | | St. Joseph High School - Lower Turf | 11:30 AM - 1 Bus - Arrive 11:30; Depart 11:45 |