Buccaneers Win 2018 Headmasters’ Challenge

The Berkeley Buccaneers kept the Cup again this year by winning the 2018 Headmasters’ Challenge between Berkeley and host Tampa Prep on Saturday, January 6, 2018. Berkeley captured the Headmasters' Trophy by a winning margin of 12.5 to 9.5 points in a closely contested event. The schools competed in 17 winter sport contests from Middle Division, junior varsity and varsity. The Buccaneers defended their 2017 victory. This marks the 15th year of the annual Headmasters’ Challenge. 

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. 
Berkeley won the Cup in 2004, 2005, 2008, 2009, 2010, 2013, 2014*, 2015, 2016, 2017 and 2018. 

*In 2014, both schools scored an equal number of points and thus the cup was shared.


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