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 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.

Tampa Prep hosted the inaugural Headmasters' Challenge on January 10, 2004. The competition began at 8:00am and continued until 4:00pm. The competition featured 15 winter sports from middle division, junior varsity and varsity.

Headmasters' Challenge Results

2004 @Tampa Prep (Winner: Berkeley Prep Score:12-7)

2005 @Berkeley Prep (Winner: Berkeley Prep Score: 11.5-8.5)

2006 @Tampa Prep (Winner: Tampa Prep Score: 15.5-4.5)

2007 @Berkeley Prep (Winner: Tampa Prep Score: 10.5-9.5)

2008 @Tampa Prep (Winner: Berkeley Prep Score: 12-9)

2009 @Berkeley Prep (Winner: Berkeley Prep Score: 17.5-3.5)

2010 @Tampa Prep (Winner: Berkeley Prep Score: 12-7)

  View pictures from the 2009 Headmasters Challenge