Berkeley Wins the Headmasters’ Challenge

The annual Headmasters’ Challenge between Berkeley Preparatory School and Tampa Preparatory School came to an exciting end on Saturday, January 10 as the Berkeley Buccaneers won the Challenge in convincing fashion with a 13-6 win that featured 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 points out of a possible 19 point total to win the coveted Headmasters’ Cup. The boys varsity soccer team sealed the Cup win for the Buccaneers with their 1-0 victory giving Berkeley its 11th point and putting the Cup out of reach for Tampa Prep.
This is the eighth 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* and 2015. 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 2016.*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.
Fans who missed the action or would like to watch a replay of the varsity competitions may do so by visiting:
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 teams from middle division, junior varsity and varsity.


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