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Winchester looks to complete perfect regular season with Thanksgiving win over host Woburn

Winchester High senior captain Bryan Harrison (54) lifts his classmate and teammate Nicky Rotondi off the ground, while celebrating one of Nicky’s explosive touchdowns against host Waltham during a game in September. Both players now hope to end their scholastic careers with a win over host Woburn for the second straight year on Thanksgiving, while also finishing up with a perfect regular season record. COURTESY PHOTO/JEN JOHNSON

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In football, Catholic Memorial was in Division 1 as late as 2019, and ironically, the school made it to the Super Bowl that year in the state’s highest division, only to lose to St. John’s Prep, 21-14 at Gillette Stadium.

It was the second straight year that the Eagles defeated them at Gillette. It was also John DiBiaso’s second year as the Knights’ coach after the legendary coach left Everett on top with Super Bowl wins in 2016 and 2017.

Then came the pandemic year, and after the MIAA (Massachusetts Interscholastic Athletic Association) navigated through it, sports returned to normal schedules with playoffs in 2021. But once the postseason rolled around in football, there was a change that significantly affected one of the state’s divisions, and it involved those Knights from West Roxbury.

DiBiaso probably knew the only way he could return to Super Bowl glory was to drop down to Division 2. The move obviously worked, much to the chagrin of schools like Winchester.

The MIAA approved the realignment change prior to the start of the 2021 campaign, and not so coincidentally Catholic Memorial has participated in the big game at Gillette four out of the last five years, including this fall after DiBiaso’s team put the hammer down on Winchester last Friday night at Medford’s Hormel Stadium, 49-0. They defeated a team that was enjoying an historic year on offense, outscoring opponents, 422-111 to come into this state semifinal game undefeated at 10-0.

But was this mismatch due to a team that should still be in Division 1?

If you ask King Philip Regional, they would probably say most definitely. The Warriors were victims of it in three out of the last four Super Bowl games. The only time they broke through was in 2023, when they took care of Marshfield in the big game, 42-14 after the Rams eliminated the Knights in the state semifinals, 52-40.

But following another Super Bowl loss to the Knights last year, King Philip decided it was time to move down a division, and it immediately paid dividends. As a result, they will now play North Attleboro in the Division 3 Super Bowl game on Dec. 5.

Naturally, Winchester High Coach Wally Dembowski was not too happy with the developments last Friday night, but is ready to put it behind him for the sake of Thursday’s annual Thanksgiving Day clash with host Woburn, starting at 10:15 a.m.

The series was all tied up prior to last year’s game at 55-55-12, but the Red & Black were able to break that stalemate with a 35-28 victory over the visiting Tanners.

Dembowski didn’t waste anytime to get his team focused away from the Catholic Memorial debacle.

“I told them right after the game that the training room is open at 7 a.m. (Saturday) to start preparing for Woburn,” he said.

But that doesn’t mean that he’s over the state semifinal loss just yet.

The veteran Winchester coach talked on a number of issues with the current playoff format, but he admits that he can only do so much.

“Alignment is out of my control. (That issue) solely rests on the athletic administration, the school (in general) and the MIAA rules regarding where schools are placed (in each division),” he said. “Right now, the Catholics and the tech schools have two Super Bowls, while the publics have three. It all depends on how the divisions are aligned, and the system isn’t about to change in the 21st century. Those state semifinalist trophies today are (only) for (this era). As far as I’m concerned, there is only one conference winner, and one Super Bowl winner.”

But the coach also says that Winchester can still control its own destiny in future postseason games.

“We need to get more players in the system, and develop them, because we don’t have the luxury that the Catholic schools have,” he said.

This year’s team just might have initiated the start of this approach.

“This is the most successful group (of Winchester High football players) in terms of wins and losses that the program has produced in the last 35-plus years,” Dembowski said. “They have accounted for two quarterfinal appearances, one trip to the state semifinals and possibly 27 wins over the past three seasons. It’s been one heck of a run. The only thing missing is a Super Bowl trophy.”

With Gianni DePrimeo on offense and Bryan Harrison on defense, along with a strong supporting cast, these players won’t be forgotten anytime soon.

A win on Thursday would at least complete the Middlesex League title in style with an undefeated record. But Dembowski knows that it won’t be easy.

“Woburn is going to throw everything at us on Thanksgiving Day after having two weeks to prepare for this game, while also having time to rest and heal up,” he said. “What I see on film and what they do will probably be different in many ways, so we’re preparing for easy communication among our players, while also playing fast at the same time. With only three days of prep work to get ready for Woburn, and limited rest after a physical game against CM, all I can say is let’s just go out there and play.”

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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