Army/Navy. Duke/North Carolina. Lehigh/Lafayette. Harvard/Yale. Deerfield/Choate. Haverford/Episcopal. Tampa Prep/Berkeley Prep.

Rivalry games! These are the games where schools that respect each other have a competitive moment, face one another and, as Michael Buffer says, "Let's get ready to rumble!"


The Headmaster's Challenge only comes once a year. It’s the day we play our peer school, a rival, in every winter sport at every grade level in one same day for The Headmasters’ Cup. We practice, we prepare, we compete, we celebrate, we cheer, we support and we have fun!

The 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. There have been 15 Headmasters' Challenges since 2004, and Tampa Preparatory School's record on the day is 4-10-1.


Many, perhaps rightly, ask, ‘Why do we have the Challenge?’  It's a good question. Part of the answer is for the historical reasons explained above. Another part of the answer is that it’s a day of celebration, a day when two communities come together, cheer for students, celebrate sport and demonstrate the breadth of their school spirit.

I am one of the most competitive people you may ever meet.  In fact, I hate to lose at anything--ever--and yes, the record appears one-sided, but what that record does not capture is what makes the day a special day for Tampa Prep and special to me. If we allow ourselves to move beyond the wins and losses and think about what sport gives a community and teaches athletes, that's where I find what’s special.

What the Challenge Really Means

Over my 11 years at Tampa Prep I have seen some incredibly special moments on this day.

  • My heart has been warmed to see a middle school girls basketball game come down to the final seconds, with a gym so loud you could not hear your own voice and you witness to that super-special-ESPN-Sports-Center moment when a young athlete makes that game-clinching basket.

  • I have seen our wrestling teams face matches where to win the points for the school--because they were out-manned--they had to win every single match and the majority had to be with a pin, and you know that they have done it more than once.  

  • I have seen soccer games as fierce as a Premier League derby in England where the passion and importance of the game is etched on the faces of every player and every fan.

  • I see the smiles, the face painting and our stickers:  GO PREP! GO RED! GO GOLD. WE ARE, TAMPA PREP! The passion and spirit I see gets the blood flowing at each and every game, regardless of the outcome.

  • On the cold days, it's the people all bundled up, with hot chocolate and coffee, cheering, catching up, supporting the kids and the school.

  • I see the alumni who have returned to cheer their alma mater, beaming with school pride. Throughout the day I love to hear our fight song (Tampa Prep: rah-rah-rah) and our alma mater song, sung together.

  • It’s also special to see the genuine friendships that exist between the two school communities. So many of the Tampa Prep and Berkeley Prep families have known one another for what seems like forever.  There are student friendships that have not only stood the test of time, but friendships that are far more durable than the competition and outcome of the day.  There are, and have been, many families with children who attended both schools and whose bond is incredibly rare, and I appreciate them.

What cannot be measured is our school spirit, the genuine interest and celebration our students show throughout the day and the gift of support and appreciation they give to one another.  Yes, the day can be measured in wins, losses and the pursuit of The Cup, but I would gladly trade The Cup for the spirit and camaraderie that has become a hallmark of who we are and how we represent the Red and the Gold.

If we do all we can, if we demonstrate the strength of our character, compete to the best of our ability and cheer and support one another, then it's a good day. If we hold The Cup, so be it. If we don't, so be it. In the end WE ARE TAMPA PREP, and the force that is “the Terrapin spirit and pride” is never in doubt!

I look forward to seeing our school shine brightly this weekend!


Kevin Plummer, Head of School