District Tournament, Tampa Catholic High School

Headmasters' Challenge logo
Join us Saturday, January 12 at Berkeley Preparatory School for the 2019 Headmasters' Challenge!

Schedule of Events

Headmasters' Challenge App

Berkley has a Headmasters’ Challenge app is available for free download for iOS phones. Simply search #HMC19 in the iOS App Store for iPhones and iPads. This app will keep you updated on event scores and the overall Headmasters Cup standings. It also provides a car locator to remind you where you parked, and a GPS-enabled map to guide you to each sporting event.

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 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 featured 15 winter sports from middle division, junior varsity and varsity.

Social Media



Make sure to share your Headmasters' Challenge pictures on social media using the #HMC19.

New this year! Follow @TP.Ernest on Facebook for updates throughout the day.

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)

2011 @ Berkeley Prep (Winner: Tampa Prep Score 10.5-9.5)

2012 @ Tampa Prep (Winner: Tampa Prep Score 13.5-6.5)

2013 @ Berkeley Prep (Winner: Berkeley Prep 12-10)

2014 @ Tampa Prep (Tied 9.5-9.5)

2015 @ Berkeley Prep (Winner: Berkeley Prep 13-6)

2016 @ Tampa Prep (Winner: Berkeley Prep 19-1)

2017 @ Berkeley Prep (Winner: Berkeley Prep 15.5 to 5.5)

2018 @ Tampa Prep (Winner: Berkeley Prep 12.5 to 9.5)