Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
WED 8/23 | 4:30 PM | Varsity | Scrimmage | Normal | Home | Glastonbury | | | | Windsor High School - Jack O'Brien Stadium | |
MON 8/28 | 4:30 PM | Varsity | Scrimmage | Normal | Home | Stratford | | | | Windsor High School - Jack O'Brien Stadium | |
THU 8/31 | 6:00 PM | Varsity | Scrimmage | Normal | Away | Cheshire | | | | Cheshire High Main Game field - Cheshire High Main Game field | |
SAT 9/9 | Postponed | Varsity | League | Postponed | Home | Bristol Central | Win | 43-0 | | Windsor High School - Jack O'Brien Stadium | |
SUN 9/10 | 10:00 AM | Varsity | League | Normal | Home | Bristol Central | Win | 43-0 | | Windsor High School - Jack O'Brien Stadium | |
MON 9/18 | 6:30 PM | Varsity | League | Normal | Home | Hall | Win | 58-22 | | Windsor High School - Jack O'Brien Stadium | |
SAT 9/23 | 2:00 PM | Varsity | Non-League | Normal | Away | New Canaan | Loss | 12-33 | | New Canaan HS - Dunning Stadium | |
FRI 9/29 | 6:30 PM | Varsity | League | Normal | Away | Middletown | Win | 27-7 | | Middletown High School - MHS Stadium | |
THU 10/5 | 7:00 PM | Varsity | League | Normal | Away | Wethersfield | Win | 42-0 | | Wethersfield High School - Cottone Field | |
FRI 10/20 | 7:00 PM | Varsity | League | Normal | Home | Newington | Win | 42-0 | | Windsor High School - Jack O'Brien Stadium | |
FRI 10/27 | 6:00 PM | Varsity | League | Normal | Away | Enfield | Win | 65-28 | | Enfield High School - EHS TURF | |
FRI 11/3 | 7:00 PM | Varsity | League | Normal | Home | Manchester | Win | 55-34 | | Windsor High School - Jack O'Brien Stadium | |
FRI 11/10 | 6:30 PM | Varsity | League | Normal | Away | Berlin | Win | 41-6 | | Sage Park - Berlin - Scalise Field -Turf Field Sage Park Stadium | |
SAT 11/18 | 1:00 PM | Varsity | League | Normal | Home | Bloomfield | Win | 53-28 | | Windsor High School - Jack O'Brien Stadium | |
TUE 11/28 | 6:30 PM | Varsity | Postseason | Normal | Home | Bunnell | Win | 41-19 | | Windsor High School - Jack O'Brien Stadium | |
SUN 12/3 | 12:30 PM | Varsity | Tournament | Normal | Home | North Haven | Loss | 0-21 | | Windsor High School - Jack O'Brien Stadium | |