Sid Tildsley Becomes Winningest Wrestler in Massachusetts History

Shawsheen Tech's senior Sid Tildlsey stamps his name in wrestling history during state finals this past week
Sid Tildsley takes the mat against his opponent
Sid Tildsley takes the mat against his opponent / Shawsheen Tech Athletics Photography

Senior wrestling captain Sidney Tildsley of Shawsheen Tech High School of Billerica, Massachusetts, just become the winningest high school wrestler in Massachusetts history.

Few names will resonate in wrestling history as much as Tildsley's. Since his career began at Shawsheen Tech, he has spent the past 3 out of 4 years competing in the 138-pound weight-class, spending only his freshman year in the 132-pound class.

During this time, Sid won the state title every single year. Yes, you read that right. Sid Tildsley has captured the Massachusetts state championship 100% of his high school career. Tildsley puts himself in elite company and, over the past four years, has been borderline unstoppable. Over his career, he has achieved some great things. His combined record throughout his freshman and sophomore years totaled 131 wins and 2 losses. He is a 4-time sectional champion, a 4-time state champion, a 4-time all-state champion, and a 3x New England Champion and owner of countless Massachusetts state records.

In his last match against Andover not to long ago, he clinched his fourth straight against Andover's Jason Ballou in just 3 minutes and 22 seconds, securing that historic fourth straight title.

Tildsley won countless invitational tournaments, such as the Lowell Holiday Tournament. Ironically, he wasn't just a winner on the wrestling mat, but he also led the Shawsheen Tech football team to a D5 Super Bowl this past fall as their starting quarterback.

Tildsley became such a dominant wrestler because of two people. His older sister, Tayla, who was a successful wrestler at the tech and National Wrestling Hall of Fame Member and Tidsley's coach until 2021, Mark Donovan. Sadly, Donovan passed away in 2021 after a battle with cancer but left his imprint on wrestling forever. After over three decades of mentoring athletes, Billerica dedicated March 19th as Coach Donovan Day in honor of the impact he left on the community.

During his time coaching at Shawsheen, he had his wrestlers in peak condition, and be respectful win or lose but still ultimate competitors, so it makes sense that he had his boys "wrestle up" in division 1. This translated into Tildsley's game; you would never find him showboating after a victory, just shaking hands with his opponent and minding his business.

Funny enough, the Tildsley wrestling bloodline doesn't end with Tayla and Sid. The youngest brother, James, recently claimed his second straight state title in the 150-pound weight class for Shawsheen as well. He went 62-0 on the year and didn't allow a single match to be decided on points.

Wrestling runs in the Tildsley's veins as you can see. Sid had an incredible run during his time at Shawsheen High School, stunning teammates and coaches along the way to making history. In honoring their late coach, Mark Donovan, the Tildsleys exemplify the connection between athlete and mentor, showcasing how personal bonds can fuel incredible achievements.


Published
Tyler Rourke
TYLER ROURKE

Tyler is a Digital Media and Journalism student at Endicott College, expected to graduate with his Bachelor's degree in 2026. He has experience covering a variety of sports for multiple newspapers. including The Salem Times and Gloucester Daily Times. He began contributing to High School On SI in 2025.