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Winchester takes its offensive show on the road to Wakefield to begin Middlesex League season Friday night

Winchester High senior linebacker and captain Bryan Harrison (54) takes down a Waltham ballcarrier during a game at Waltham on Sept. 19. COURTESY PHOTO/JEN JOHNSON

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Domination was the operative word of the month for the Winchester High School football team. Throughout their three September games, the Red & Black (3-0) have outscored the opposition, 140-36. Breaking it down even further, they took care of both Peabody and Waltham by identical 42-7 scores, before beating up Masco, 56-22 to close out the month on Sept. 26.

But now, the calendar has flipped to October, and Coach Wally Dembowski’s team is about to begin the Middlesex League schedule against host Wakefield tonight (Oct. 3) at 6 p.m.

Dembowski predicts that this game should be another dogfight at Landrigan Field between two longtime rivals.

“After watching (game) film on (Wakefield), they will be the most physically aggressive team that we’ve played against to this point,” the coach said. “They run the ball hard, and have a solid passing attack, while getting off the ball very well. They have a good run defense with multiple fronts.”

Winchester senior quarterback Ronan O’Connell directs his teammates prior to the snap during a game against host Waltham on Sept. 19. COURTESY PHOTO/JEN JOHNSON

Here’s one more look at last Friday night’s home game against Masco. The Winchester offense continued to run the ball extremely well with no turnovers, while the defense created three takeaways with two interceptions and one fumble recovery. As a whole, the unit limited Masco’s run game to 67 yards on 28 carries.

Senior captain Gianni Deprimeo was Winchester’s leading rusher with 16 carries for 290 yards and five touchdowns. His classmate Nicky Rotondi ran for 120 yards on eight carries. Altogether, the Red & Black accounted for 481 yards on the ground.

Will Mango was one of the leaders on defense against the Chieftains with six solo tackles, three assisted stops and one sack. Ted Budreski had five tackles. Will Bolognese, who is also the team’s reliable placekicker, was credited with three tackles and one interception. On offense, he was a perfect eight-for-eight in extra points.

The Winchester scoring plays against the Chieftains were evenly distributed. They accounted for two touchdowns in each of the four quarters.

Rotondi got the offensive going with a 24-yard touchdown run, and Bolognese then nailed his first of eight successful extra point tries.

After Masco came back to tie up the proceedings at seven apiece, the Red & Black scored the next two touchdowns. Deprimeo had them both on runs of 13- and 2-yards. The Chieftains, however, scored again to trim the deficit to six, 21-15. But Deprimeo got it right back from 27 yards away to close out the first half offense.

Winchester senior wideout Nicky Rotondi (3) scores a touchdown against host Waltham during the Sept. 19 game. COURTESY PHOTO/JEN JOHNSON

It was a 28-15 game at halftime, and the Winchester boys added to their lead, when Deprimeo busted one 80-yards early on in the third quarter.

The Chieftains then accounted for another touchdown, but were still losing by two scores, 35-22.

Winchester finished off the game in style with three unanswered touchdowns. Nolan Byrne’s 31-yard run to paydirt started it off, followed by a Rotondi 21-yard touchdown jaunt and another one by Deprimeo, his fifth of the game, this time from the 22.

Joe McConnell is a longtime, award-winning sports editor for numerous North Shore publications. He began covering Winchester sports for the News last November.

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 2025 Winchester News Group, Inc. Copying and sharing with written permission only.

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