Buccaneers Claim Seventh Consecutive Headmasters’ Challenge Victory

The Berkeley Preparatory School Buccaneers won the 2019 Headmasters’ Challenge between Berkeley and cross-town rival Tampa Preparatory School in convincing fashion on Saturday, January 12 as the Buccaneers won 15.5 to 5.5 in combined totaled points. This year’s victory follows another exciting win after last year’s victory over Tampa Prep. This marks the seventh consecutive Headmasters’ Cup title for Berkeley.

The annual contest featured 16 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 11 points out of a possible 21 points to win the coveted Headmasters’ Cup.

This is the 11th 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, 2016, 2017, 2018, and 2019. The cup will now stay at Berkeley for a year until the next Headmasters’ Challenge in 2020.

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


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