Skip to content

Winchester Red & Black football begins the 2026 season tonight at home against non-league Lynn Classical

The Winchester High football team poses proudly with the state Final Four banner and trophy last year after beating Lincoln-Sudbury in an Elite 8 Division 2 game at Knowlton Stadium, 38-21. Many of these players have since graduated, but for those who remain, they hope to extend the varsity team’s streak for winning seasons to four straight years. COURTESY PHOTO/JEN JOHNSON

Table of Contents

When the Winchester Red & Black football team squares off against non-league Lynn Classical tonight (Sept. 10, 6:30 p.m.) in the home opener at Knowlton Stadium, fans will see a whole bunch of new faces in the starting offensive and defensive lineups.

Last year’s club put together a season that won’t soon be forgotten by those same fans, who cheered them on to a 10-0 start that included two wins in the Division 2 playoffs. As the fourth seed, the Winchester boys went on to defeat North Quincy (42-6) and Lincoln-Sudbury (38-21), before getting shutout by top seed Catholic Memorial in the state semifinal round.

To get that far, they were awarded with the Final Four trophy and banner. They then wasted little time to get back on the winning track, beating Thanksgiving rival Woburn, 28-14, which resulted in a final overall record of 11-1.

All of that winning secured for them the Middlesex League title, their first in 35 years. It was an all-around, entertaining effort, with the offense leading the charge, racking up 450 points in 12 games. The defense was also equally impressive, allowing just 160 points.

League MVP and two-time All-Scholastic Gianni DePrimeo was the star of this show, while quarterback Ronan O’Connell consistently engineered the offense downfield.

Coach Wally Dembowski, who’s entering his 16th year along the Winchester sidelines, understands it’s difficult to repeat that much success, but that doesn’t mean that they can’t have another winning campaign. But he knows like in any other season, good health is a prerequisite for success.

“We need to stay healthy and compete on every play (to once again produce winning results),” he said.

The Red & Black returns just one offensive starter, and three more on defense, while special teams have two back that includes long snapper Cole Deason and kicking specialist Will Bolognese.

Bolognese, a 2026 captain, made the All-League and All-Star teams one year ago as a proficient kicker. He also intercepted five passes on defense as a free safety that resulted in touchdowns.

“We have players on this team, who had the opportunity to play last year, and will now be counted on to start, while also helping to lead the team to its fourth consecutive winning season,” said Dembowski. “Patrick Wynn is the lone returnee on the offensive line, and he will be lined up with seniors Evan Berg and Ciaran Hannon, and juniors Jack Lennon and Ben Adams. They will be asked to protect quarterback Peter Alexopoulos, who is also one of this year’s captains.”

The offensive backfield will be made up of captain Dominic Vozzella, and juniors Eyitayo Owolabi and Leo Lamont. Together, they hope to minimize the loss of DePrimeo, who’s now a lacrosse player at the U.S. Naval Academy.

Sophomore tight end and middle linebacker Henry Nagler is scheduled to fill the all-star shoes of Bryan Harrison, who’s now a linebacker on the Harvard University football team, not to mention Mike Ficociello, who’s now a tight end at Bates College in Maine.

Ted Budreski and Ryan Martin were the go-to wide receivers in 2025, but they too have since graduated. Looking to make up for that loss production will be the likes of seniors Andrew Haigis and Keith Galvin, as well as sophomore Zayne Osman. Seniors Gibson Ketterer and Christaki Kolias, who are newcomers to the program, will add depth to this critical offensive position.

Captain Eddie Sim, Eyitayo Owowlabi and Nagler are scheduled to be the team’s linebackers, while aforementioned Bolognese will call the shots in the defensive backfield. Kolias, Galvin, Haigis and Osman are slated to be the cornerbacks. Haigis, Bolognese, Vozzella, Ketterer, Katz and Tarabelsi will alternate as safeties. Sophomore Pierre Bodo, Berg, Wynn, Adams and Lennon will be along the defensive line.

All of this just might add up to the varsity team’s fourth straight year with a winning record, and it all begins once again tonight (Sept. 10, 6:30 p.m.) against non-league Lynn Classical at Knowlton.

Joe McConnell is a longtime, award-winning sports editor for numerous North Shore publications. He began covering Winchester sports for the News in November 2024 and is currently its Sports Editor. He can be reached at editor@winchesternews.org.

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.

Latest

Winchester Health Department to hold public flu, COVID clinics

Winchester Health Department to hold public flu, COVID clinics

The following was submitted by the Winchester Health Department: The town of Winchester’s Health Department will be holding public flu and COVID clinics during the month of October. Clinics will be held on the following Thursdays: Oct. 1, Oct. 15 and Oct. 22, from 5-7 p.m., at

  Subscribe