Winchester High School has cruised to a 6-0 start, looking dominant in every phase of the game.

Wally Dembowski took over the football program in 2011. He has coached many great squads in the past, but this one might just be on a different level.

“I think they just enjoy each other’s company,” Dembowski said of his group. “Each day in practice, it’s competitive.”

For Dembowski, the last time he could remember one of his teams receiving this much praise was 2019, when Winchester reached the Div. 3 North final under the MIAA’s old playoff system.

In 2025, the Red and Black have averaged 43.2 points per game. They have knocked off a series of successful squads convincingly, most notably Masconomet (a 56-22 win Sept. 26) and Wakefield (a 42-7 romp Oct. 3). This past Friday, the school pull

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