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Another high school sports year is less than a week away. On Monday, Aug. 24, the Winchester High fall athletes will report to their coaches for the first day of practice.
The football team for one will be heading into this season looking to repeat as Middlesex League champions after the 2025 squad snapped a 35-year drought between titles for the program.
Coach Wally Dembowski had much to say about that historical season following his team’s second straight win over traditional Thanksgiving foe Woburn.
“The season was fantastic,” Dembowski said immediately after the 2025 campaign. “Our 11 wins (9-0 in the regular season, 2-1 in the playoffs) this year tied a school record, and the players worked extremely hard to get the job done, while the coaches were able to push them past their comfort levels. One of our goals this year was winning the league. Done. Another one was to go deeper in the playoffs beyond the quarterfinals (wins over North Quincy, 42-6; Lincoln-Sudbury, 38-21). Done. Thanksgiving was another goal. Done. We also wanted to win the Super Bowl, but CM unfortunately got in the way.”
But it’s time to turn the page with the 2026 season right around the corner.
First up for the Red & Black will be a joint home practice at Ciarcia against Lynn English on Sept. 1, at 5:30 p.m. in order to get ready for the home opener against non-league Lynn Classical at Knowlton on Sept. 10 at 6:30 p.m.
They will then face non-league host Acton-Boxborough on Friday night, Sept. 18, at 7 p.m., before going to Boxford to square off against host Masconomet on Friday, Sept. 25, at 6:30 p.m., setting the stage for the Middlesex League opener at Melrose on Oct. 2 at 7 p.m.
The road warriors will remain on the bus for a trip to Reading to play the Rockets on Oct. 9 at the same time. They will then finally come home to Knowlton after a four-week absence to host the Arlington Spy Ponders on Oct. 16 at 6:30 p.m. Lexington will follow the Spy Ponders to Knowlton for a game on Thursday, Oct. 22, again at 6:30 p.m.
The last regular season game before the Division 2 playoffs begin will be against host Belmont on Friday, Oct. 30, at 6 p.m. The Thanksgiving Day clash against rival Woburn will be at home this year on Nov. 26 at 10:15 a.m.
That game is still three months away, but once there Dembowski’s boys will be seeking their third straight triumph over the Tanners.
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.
