Buccaneers Rule the Day at Headmasters’ Challenge

The Berkeley Preparatory School Buccaneers won the 2016 Headmasters’ Challenge between Berkeley and Tampa Preparatory School in convincing fashion on Saturday, January 9 as the Buccaneers won the Challenge 19-1 in combined totaled points. The Terps only point was earned as a result of a tie in boys soccer following a weather-related game cancellation where the two teams had to split the points. This year’s victory follows another convincing win after last year’s 13-6 victory over Tampa Prep in the annual contest that features 14 winter sports from middle division, junior varsity and varsity teams. Two points were awarded to varsity winners and one point was awarded to sub-varsity winners. The points were tallied throughout the day, and the winning school needed at least 10.5 points out of a possible 20 points to win the coveted Headmasters’ Cup. This was the first time in cup history that a school won every completed competition.

This is the ninth time Berkeley has won or shared the Cup in the history of the competition. Berkeley won the Cup in 2004, 2005, 2008, 2009, 2010, 2013, 2014*,2015 and 2016. Tampa Prep won the Cup in 2006, 2007, 2011, 2012 and 2014*. The cup will now stay at Berkeley for a year until the next Headmasters’ Challenge in 2017.
*In 2014, both schools scored an equal number of points and thus the cup was shared.
Click here for scores and results of each competition.
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 for which the schools would compete 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 featured 15 winter sports from middle division, junior varsity  and varsity teams.


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