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Winchester football snaps two-game losing streak with win over Arlington

Winchester High football Coach Wally Dembowski talks to the team after last Friday night’s convincing win over Arlington, 38-14 at Knowlton Stadium. WINCHESTER NEWS STAFF PHOTO / JACKSON LEWIS

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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 damp Knowlton Stadium, where they beat Arlington (2-4) handily, 38-14.

Prior to the Arlington game, the Red & Black were the 13th seed in the MIAA Division 2 power rankings, but the 24-point victory over the Spy Ponders will undoubtedly move them up in the postseason standings.

It didn’t take the Winchester boys long to turn things back around. On Arlington’s first snap, senior captain Will Bolognese came down with an interception, and the offense took it from there, when senior quarterback Peter Alexopoulos appropriately found Bolognese in the end zone for a 32-yard touchdown.

“We challenged these guys,” Coach Wally Dembowski said after the game. “We practiced a little bit harder on Monday, Tuesday and Wednesday of this week, and that certainly helped, because (Arlington is) a little bigger than we are.”

Arlington tied up the game late in the first quarter on a strong run by senior Ryan Scull, but after that it was all Winchester.

The second quarter belonged to the home team.

Alexopoulos first scored on an 11-yard keeper. After the defense stopped Arlington on just three downs, he then hooked up with Bolognese again for a 33-yard scoring strike on fourth down. Bolognese followed up those two scores with a 65-yard punt return to the endzone to extend the lead to 28-7.

Arlington senior captain Alexi Trapotsis trimmed the deficit in half, when he was on the receiving end of a 15-yard touchdown pass from quarterback Joey Schiano with just 24 seconds left in the first half.

But Winchester sophomore kicker Zayne Osman quickly answered back with a 40-yard field goal as time expired to give his teammates a 31-14 lead at the break. He also nailed five extra points in as many attempts after each one of his team’s touchdowns.

Dembowski had a lot of praise for the team after this win.

“Our skill kids really stepped it up (against Arlington), and they played really well,” he said. “It was also good to see some explosive plays.”

That explosiveness was evident on the last scoring drive of the game, when the home team was backed up on its own seven with the rain pouring down on the Knowlton turf. Alexopoulos, not bothered by the weather, ran like the wind, covering 93-yards for six points.

The defense then took over to shutdown Arlington for the rest of the game. Senior captain Eddie Sim and Patrick Winn both combined for sacks to lead that effort, while Dominic Vozzella stood out on both sides of the ball throughout the entire game.

Dembowski knows that it will only get more interesting as the intensity ramps up with the playoffs right around the corner.

“When we went to the playoffs last year, the competition got a little bit hotter,” he said, “and so we know we need to keep that intensity level up over the next two weeks (to make sure we get back there).”

This week, Lexington comes to Knowlton on Thursday night (Oct. 22, 6:30 p.m.). It will also be Senior Night, where the team’s 19 seniors will be honored before the start of another league clash.

Following the game, the Red & Black will get ready to play host Belmont on Oct. 30 at 6 p.m., with the playoffs beginning seven days later.

Jackson Lewis is a journalism student at Boston University. This story is part of a partnership between Winchester News and the Boston University Department of Journalism’s Newsroom program.

Winchester News is a non-profit organization supported by our community. If you appreciate having local Winchester news, please donate to support our work, and subscribe to our free weekly newsletter. Copyright 2026 Winchester News Group, Inc. Copying and sharing with written permission only.

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