| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/31 | 10:00 AM | Varsity | Scrimmage | Normal | Away | Amity | | | | New Milford High School - Joe Wiser Stadium - NMHS | 7:45 AM - 2 Buses |
| Brookfield | | |
| New Milford | | |
| THU 9/5 | 4:00 PM | Varsity | Scrimmage | Normal | Away | Darien | | | | Darien High School - DHS Stadium East | 2:45 PM - 2 Buses |
| FRI 9/13 | 7:00 PM | Varsity | Non-League | Normal | Away | Notre Dame-West Haven | Loss | 13-33 | | Veterans Memorial Park (West Haven, CT) - Field | 4:00 PM - 2 Buses |
| FRI 9/20 | 7:00 PM | Varsity | League | Normal | Away | Danbury | | | | Danbury High School - Stadium Turf Field | 3:45 PM - 2 Buses |
| FRI 9/27 | 7:00 PM | Varsity | Non-League | Normal | Home | Fairfield Prep | | | | Trumbull High School - McDougall Stadium | |
| SAT 10/5 | 7:00 PM | Varsity | League | Normal | Away | Ridgefield | | | | Ridgefield High School - Tiger Hollow Stadium | 3:15 PM - 2 Buses |
| FRI 10/18 | 7:00 PM | Varsity | League | Normal | Home | Brien McMahon | | | | Trumbull High School - McDougall Stadium | |
| FRI 10/25 | 7:00 PM | Varsity | League | Normal | Home | Greenwich | | | | Trumbull High School - McDougall Stadium | |
| FRI 11/1 | 7:00 PM | Varsity | League | Normal | Home | Stamford | | | | Trumbull High School - McDougall Stadium | |
| SAT 11/9 | 1:00 PM | Varsity | League | Normal | Away | Westhill | | | | Westhill High School - J. Walter Kennedy Stadium | 8:15 AM - 1 Bus |
| FRI 11/15 | 7:00 PM | Varsity | League | Normal | Home | Staples | | | | Trumbull High School - McDougall Stadium | |
| THU 11/28 | 10:30 AM | Varsity | League | Normal | Away | St. Joseph | | | | St. Joseph High School - Upper Turf | 8:30 AM - 2 Buses |