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It’s definitely an understatement to say that Winchester is synonymous with tennis, and on the high school front, both the boys and girls teams have done their jobs to live up to that reputation over the years.
So far this spring, the boys have maintained that perception with an 8-2 record. The girls are also 8-2 after 10 matches. As of May 2, the boys are seeded 13th in the Division 1 power rankings, while the girls are ranked 11th.
The Red & Black boys were 12-6 throughout the regular season last spring, and ended up as the 12th seed in the Division 1 power rankings. In the postseason, they first defeated Boston Latin, the 21st seed, 4-1 in the Round of 32, before losing a close match to BC High, the fifth seed, in the Sweet 16, 3-2. But the Eagles then fell to Lexington in the Elite 8, 4-1. St. John’s Prep ended up winning the 2025 Division 1 state title, beating Concord-Carlisle, 4-1.
Winchester has also had its share of state conquests, the last one coming in 2018 when that team won the Division 2 EMass state title. Prior to that, the 2016 club also came out on top in the Division 2 EMass finale.
Boys tennis didn’t become a sanctioned high school sport until 1967, and 10 years later in 1977 Winchester took home its first state championship in Class A at the time. They won it all again in 1981, this time in Division 1.
From 2003-2009, the team rattled off seven straight Division 2 state conquests. The varsity team won it again in 2011, also in Division 2, just before those aforementioned 2016 and 2018 titles. The Red & Black returned to Division 1 in 2022.
“Winchester is a big tennis town, so I attribute much of the program’s past successes to the community’s interest in the sport,” said Mike Lauretano, now in his fourth year as the high school program’s boys head coach.
Lauretano has 17 players on this year’s varsity roster, and seniors Jeffrey Chen, Thomas Andrews, Jamie Binda-Dunn and Sam Song are the team’s 2025 captains.
The veteran coach is pleased to have the large numbers.
“We are fortunate to have an abundantly deep team,” said Lauretano. “Everyone on the roster has proven that they belong here after a rigorous and competitive tryout, and as a result they have great team chemistry, while also knowing how to push each other to be at their very best every time they step on the court.”
Among the talented varsity personnel, freshman Henry May has really surprised the coach the most.
“I knew that Henry was a strong player when he came out for tryouts this spring, but did not expect him to end up playing first singles for us,” Lauretano added.
Despite the solid winning record, Lauretano admits there have been a few close matches, including another narrow loss to BC High, 3-2 in the home opener back on March 31.
“We hope to turn that score around when we play them again to close out the regular season at their place on May 20,” said Lauretano.
In the Middlesex League, the Winchester coach knows that Lexington is once again the team to beat. On April 16, they lost to the host Minutemen, 4-1. But like BC High, the Winchester boys also get another crack at their league rivals when they come to the Packer Courts on May 14.
Besides May at first singles, the rest of the starting lineup includes second singles player Carl Stredicke with Song at third singles. The first doubles team is comprised of Andrews and Binda-Dunn, while Kadhir Kumeran and Chen make up second doubles.
The Red & Black have three home matches next week at the Packer Courts, starting with Watertown on Monday, May 5, beginning at 4:15 p.m., followed by Burlington (May 7, 4 p.m.) and Arlington (May 9, 4:15 p.m.).
