The 2020 Headmasters’ Challenge between Berkeley Preparatory School and Tampa Preparatory School will be held on Tampa Prep's campus on Friday, January 10 and Saturday, January 11, 2020. The schools will compete in 3 winter sports and 15 contests from Middle Division, junior varsity and varsity; the Buccaneers hope to defend their 2019 victory in capturing the cup over their cross-town rival. This marks the 17th year of the annual Headmasters’ Challenge. Scroll down for a complete schedule of events.
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 and 2019. 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.