The 2022 Headmasters’ Challenge between Berkeley Preparatory School and Tampa Preparatory School will be held on Berkeley Preparatory School's campus on Friday, January 7 and Saturday, January 8, 2022. The schools will compete in 3 winter sports and 15 contests from Middle Division, junior varsity and varsity; the Buccaneers hope to defend their 2020 victory in capturing the cup over their cross-town rival. This marks the 18th 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, 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.
Note: In 2021, the Headmasters' Challenge did not take place due to COVID-19.