| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/26 | 2:00 PM | Varsity | Scrimmage | Normal | Away | Fairfield Prep | | | | Fairfield University - Rafferty Stadium | 12:00 PM - 2 Buses - Arrive 12:00; Depart 12:10 |
| THU 8/31 | 6:00 PM | Varsity | Scrimmage | Normal | Home | Notre Dame-West Haven | | | | Ridgefield High School - Tiger Hollow Stadium | |
| FRI 9/8 | 7:00 PM | Varsity | Non-League | Normal | Home | Cheshire | Loss | 10-39 | | Ridgefield High School - Tiger Hollow Stadium | |
| THU 9/14 | 7:00 PM | Varsity | League | Normal | Away | Staples | Loss | 3-42 | | Staples High School - Staples Stadium | 4:30 PM - 2 Buses - Arrive 4:30; Depart 5:00 |
| FRI 9/22 | 7:00 PM | Varsity | League | Normal | Away | West Haven | Loss | 7-42 | | Veterans Memorial Park (West Haven, CT) - Field | 3:00 PM - 2 Buses - Arrive 3:00; Depart 3:30 |
| SAT 9/30 | 2:00 PM | Varsity | League | Normal | Home | Trumbull | Loss | 21-42 | | Ridgefield High School - Tiger Hollow Stadium | |
| FRI 10/13 | 6:00 PM | Varsity | League | Normal | Away | Fairfield Ludlowe | Loss | 44-53 | | Fairfield Ludlowe High School - Taft Field | 3:30 PM - 1 Bus - Arrive 3:30; Depart 4:00 |
| FRI 10/20 | 7:00 PM | Varsity | League | Normal | Home | St. Joseph | Loss | 7-30 | | Ridgefield High School - Tiger Hollow Stadium | |
| FRI 10/27 | 7:00 PM | Varsity | League | Normal | Home | Westhill | Win | 21-6 | | Ridgefield High School - Tiger Hollow Stadium | |
| FRI 11/3 | 7:30 PM | Varsity | League | Normal | Home | Stamford | Loss | 7-37 | | Ridgefield High School - Tiger Hollow Stadium | |
| FRI 11/10 | 7:00 PM | Varsity | League | Normal | Away | Greenwich | Loss | 0-35 | | Greenwich High School - Cardinal Stadium | 4:00 PM - 2 Buses - Arrive 4:00; Depart 4:30 |
| WED 11/22 | 6:00 PM | Varsity | League | Normal | Away | Danbury | Win | 21-7 | | Danbury High School - Stadium Turf Field | 4:00 PM - 3 Buses - Arrive 4:00; Depart 4:15 |