The 2022 Headmasters’ Challenge between Berkeley Preparatory School and Tampa Preparatory School marked the eighth consecutive year the Buccaneers have won or shared the cup. Berkeley hosted this year's Headmasters' Challenge on Friday, January 7, and Saturday, January 8, 2022. The competition featured 15 separate winter sports with student-athletes representing Middle Division, junior varsity, and varsity teams. Winning points were tallied throughout the day. This year, the Buccaneers "kept the cup" winning a convincing 13-7 point victory.

History of the Headmasters’ Challenge

Remembering the intense rivalry between Deerfield Academy (where Tampa Prep’s former Headmaster Gordon MacLeod taught) and Choate (where Berkeley’s former Headmaster Joseph Merluzzi taught), Mr. MacLeod suggested that a similar day be developed between Tampa Prep and Berkeley. Mr. Merluzzi readily agreed, acknowledging the fun and good competition that resulted from the Deerfield-Choate Day and the possibility for Tampa Prep and Berkeley to have the same experience.
The pact was cemented with a clink of water glasses, and so the Headmasters’ Challenge began. The prize the schools would compete for was the Headmasters’ Cup, which would reside at the winning school for the year. The inaugural Headmasters’ Challenge was hosted by Tampa Prep on January 10, 2004. The competition began at 8 a.m., and continued all day until 4 p.m. The competition featured 16 winter sports teams from Middle Division, junior varsity and varsity.
Berkeley won the Cup in 2004, 2005, 2008, 2009, 2010, 2013, 2014*, 2015, 2016, 2017, 2018, 2019, 2020, and 2022. Tampa Prep won the Cup in 2006, 2007, 2011, 2012, and 2014*.

*In 2014, both schools scored an equal number of points and thus the cup was shared.
Founded in 1960, Berkeley is an independent, Episcopal, college-preparatory day school located in Tampa, FL, for boys and girls in grades Pre-Kindergarten through 12. Approximately 1,400 students gather here from the greater Tampa Bay area to form ONE Berkeley.