Red & Black Roll Early, Eye Redemption Against Lexington

Author: Tommy Kowalczuk WHS Class of '26

The Winchester boys varsity tennis team has come out firing this season, posting an impressive 8–1 record and establishing themselves as a serious contender in the league. Signature wins over Belmont High, Cambridge Rindge and Latin, and Reading High have highlighted just how dangerous this Red & Black squad can be when it finds its rhythm.

Leading the charge at first singles is sophomore Henry May, who has been nearly flawless so far. May’s success isn’t just about clean winners—it’s about pressure. Match after match, he’s shown an ability to drag opponents into uncomfortable rallies, exposing weaknesses and forcing errors. While some players fade as matches wear on, May does the opposite, thriving in second and third sets as his opponents struggle to maintain their level.

At second singles, senior captain Carl Stredicke has been just as vital. Known for his dominant serve-plus-one pattern, Stredicke controls points early with heavy groundstrokes that have only grown more consistent as the season progresses. He’s currently working through a minor wrist injury, but the team remains hopeful he’ll return in time for the highly anticipated rematch against Lexington—the only team to hand Winchester a loss this season.

That defeat to Lexington stands out not just because it’s the lone blemish, but because of how it happened. Winchester was swept across the board in straight sets, with the Minutemen controlling every match. It’s a result the Red & Black haven’t forgotten.

Elsewhere in the lineup, Winchester has shown depth and flexibility. Senior captain Tommy

Kowalczuk has delivered key wins at third singles, while the doubles teams have been equally reliable. Juniors Uberto Manganaro and Evan Wei have built strong chemistry at first doubles, and senior captain Ahdvey Karthikeyan alongside sophomore Ethan Tan have produced consistent results at second doubles.

As the team continues to experiment with its lineup, Friday’s rematch against Lexington could feature a notable shift, with Manganaro expected to step into the third singles spot. The adjustment reflects Winchester’s willingness to adapt—and its determination to flip the script.

With momentum on their side and a clear target ahead, the Red & Black aren’t just looking to win—they’re looking for payback