| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/26 | 10:00 AM | Varsity | Scrimmage | Normal | Away | Bullard-Havens Tiger Pride | | | | Kennedy Stadium (Bridgeport) - Kennedy Stadium (Bridgeport) | |
| Brien McMahon | | |
| Platt Tech | | |
| THU 8/31 | 4:30 PM | Varsity | Scrimmage | Normal | Away | Holy Cross | | | | Municipal Stadium Complex (Waterbury, CT) - Ray Snyder, Sr. Turf Field | |
| FRI 9/8 | 7:00 PM | Varsity | League | Normal | Away | Foran | Loss | 12-37 | | Foran High School - Foran High School - Turf Field | |
| FRI 9/22 | 6:00 PM | Varsity | League | Normal | Home | Bristol Eastern | Loss | 0-2 | | Bowen Field - Football Field | |
| FRI 9/29 | 5:00 PM | Varsity | League | Normal | Home | Daniel Hand | Loss | 0-17 | | Bowen Field - Football Field | |
| FRI 10/6 | 7:00 PM | Varsity | League | Normal | Away | Guilford | Win | 20-14 | | Guilford High School - Kavanaugh Turf Field and Track | |
| FRI 10/13 | 6:00 PM | Varsity | League | Normal | Home | Lyman Hall | Win | 26-7 | | Bowen Field - Football Field | |
| FRI 10/20 | 6:00 PM | Varsity | League | Normal | Home | Harding | Loss | 6-12 | | Bowen Field - Football Field | |
| FRI 10/27 | 6:00 PM | Varsity | League | Normal | Away | Fitch | Loss | 13-51 | | Fitch High School - Dorr Field (Football Field on Campus) | |
| FRI 11/3 | 7:00 PM | Varsity | League | Normal | Away | East Haven | Win | 27-26 | | East Haven High School - EHHS Turf Field & Track | |
| FRI 11/17 | 6:00 PM | Varsity | League | Normal | Home | Bassick | Win | 52-8 | | Bowen Field - Football Field | |
| THU 11/23 | 10:30 AM | Varsity | League | Normal | Away | Wilbur Cross | Win | 62-6 | | Wilbur Cross High School - Wilbur Cross Athletic Complex | |