| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/26 | 10:00 AM | Varsity | Scrimmage | Normal | Home | Brien McMahon | | | | Kennedy Stadium (Bridgeport) - Kennedy Stadium (Bridgeport) | |
| Hillhouse | | |
| Platt Tech | | |
| WED 8/30 | 4:30 PM | Varsity | Scrimmage | Normal | Home | Kennedy | | | | Kennedy Stadium (Bridgeport) - Kennedy Stadium (Bridgeport) | |
| SAT 9/9 | 3:30 PM | Varsity | Non-League | Normal | Home | Pomperaug | Loss | 7-42 | | John F Kennedy Stadium - John F Kennedy Stadium | |
| SAT 9/16 | 10:00 AM | Varsity | League | Normal | Home | O'Brien Tech | Win | 27-0 | | Kennedy Stadium (Bridgeport) - Kennedy Stadium (Bridgeport) | |
| FRI 9/22 | 6:00 PM | Varsity | League | Normal | Away | Cheney Tech | Win | 14-6 | | Cheney Tech. - Football Field | |
| FRI 9/29 | 5:00 PM | Varsity | League | Normal | Away | Northwest United | Loss | 14-21 | | Nonnewaug High School - Turf Field | |
| THU 10/12 | 4:00 PM | Varsity | Non-League | Normal | Away | Bassick | Win | 51-12 | | Kennedy Stadium (Bridgeport) - Kennedy Stadium (Bridgeport) | |
| THU 10/19 | 6:00 PM | Varsity | League | Normal | Home | Quinebaug Valley Pride | Win | 23-6 | | John F Kennedy Stadium - John F Kennedy Stadium | |
| THU 10/26 | 7:00 PM | Varsity | League | Normal | Home | VGW TECHS | Win | 56-0 | | John F Kennedy Stadium - John F Kennedy Stadium | |
| FRI 11/3 | 6:30 PM | Varsity | League | Normal | Away | Wilcox Tech | Win | 18-10 | | Falcon Field (Meriden, CT) - Football Field | |
| SAT 11/11 | 12:00 PM | Varsity | League | Normal | Away | Prince Tech-Innovation | Win | 14-0 | | Prince Tech High School - Prince Tech/Moriarty Field | |
| FRI 11/17 | 7:00 PM | Varsity | League | Normal | Home | ATI | Loss | 14-28 | | John F Kennedy Stadium - John F Kennedy Stadium | |