Winchester football stages comeback to beat North Quincy in first round of playoffs
Red & Black will play Chelmsford in Elite 8 on Nov. 13
Jackson Lewis | Correspondent
Winchester football begins D-2 Super Bowl playoffs tonight against North Quincy at Quincy’s Veterans Memorial Stadium
The Winchester High football team is cruising into the Division 2 Super Bowl playoffs after easily dispatching host Belmont last Friday night, 35-0. Since then, they have been preparing for North Quincy, a familiar opponent that they defeated in the Round of 16 last year at home, 42-6.
With playoffs looming, Winchester football coach Wally Dembowski discusses forfeit win over Lexington, intrasquad scrimmages, power rankings
The Winchester High Red & Black football team (5-2) had an action-packed Senior Night planned ahead of its seventh game of the season. However, Middlesex League rival Lexington had to forfeit Thursday night’s (Oct. 22) game at Knowlton Stadium, because it was unable to safely field a
Winchester football snaps two-game losing streak with win over Arlington
After losing two straight Middlesex League games on the road to Melrose and Reading, the Winchester High School football team (4-2) had to right the ship quickly to stay in playoff contention. And they did just that, and they did it fast last Friday night (Oct. 16) at a
Fall into Books: Winchester hosts its 32nd Annual Authorfest
For two days and two days only, books will take center stage in Winchester as students and families get the special chance to meet the writers and illustrators behind some of their favorite novels. Winchester’s Authorfest returns Oct. 14 and 15 for its 32nd year, bringing 17 authors to
Winchester football loses competitive battle to host Melrose
The three-game winning streak is over, but not without a fight. The Winchester Red & Black football team (3-1) invaded Melrose’s Fred Green Memorial Field (Oct. 2 to trade punches with its Middlesex League rivals, but when the game reached its most decisive moments, the visitors couldn’
Winchester High School football pummels Lynn Classical in the home opener
Coach Wally Dembowski couldn’t have asked for a better way to start the 2026 season after his Winchester High football team dismantled the Lynn Classical Rams at Knowlton Stadium on Sept. 10, 38-6. There were a whole bunch of new faces in the starting lineups for the Red