The 2019 Headmasters’ Challenge between Berkeley Preparatory School and Tampa Preparatory School will be held on Berkeley's campus on Saturday, January 12, 2019. The schools will compete in 3 winter sports and 16 contests from Middle Division, junior varsity and varsity; the Buccaneers hope to defend their 2018 victory in capturing the cup over their cross-town rival. This marks the 16th year of the annual Headmasters’ Challenge. Scroll down for a complete schedule of events.

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 the schools would compete for 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 began at 8 a.m., and continued all day until 4 p.m. The competition featured 16 winter sports teams from Middle Division, junior varsity and varsity.
 
Berkeley won the Cup in 2004, 2005, 2008, 2009, 2010, 2013, 2014*, 2015, 2016, 2017, 2018 and 2019. Tampa Prep won the Cup in 2006, 2007, 2011, 2012 and 2014*.

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

Schedule of Events

January 12, 2019

9:00 Basketball: Middle Division Girls White
Johnson Field House
9:00 Basketball: Middle Division Boys Navy B
Dimmitt Gymnasium
9:00 Soccer: Middle Division Girls White
Dickey Field
9:00 Wrestling: Varsity
Straz Family Field House - Weigh-in 8 AM
9:30 Soccer: JV Boys
Newman Stadium
10:00 Basketball: Middle Division Boys Blue
Johnson Field House
10:00 Basketball: Middle Division Girls Navy
Dimmitt Gymnasium
10:30 Soccer: Middle Division Girls Navy
Dickey Field
10:30 Basketball: JV Boys
Straz Family Field House
11:00 Basketball: Middle Division Boys White
Johnson Field House
11:00 Basketball: Middle Division Boys Navy A
Dimmitt Gymnasium
11:00 Soccer: Varsity Girls
Newman Stadium
12:00 Soccer: JV Girls
Dickey Field
12:00 Basketball: Varsity Girls
Straz Family Field House
1:00 Soccer: Varsity Boys
Newman Stadium
1:30 Basketball: Varsity Boys
Straz Family Field House

Scoring: 2 points for Varsity Wins; 1 point for sub-varsity wins

BERKELEY PREPARATORY SCHOOL

4811 Kelly Road
Tampa, FL 33615
(813) 885-1673