The 2017 Headmasters’ Challenge between Berkeley Preparatory School and Tampa Prep will be held on Berkeley's campus on Saturday, January 7, 2017. The competition, with events scheduled from 8:00 a.m. to 2:30 p.m., will feature 16 winter sports from Middle Division, junior varsity, and varsity teams. Winning points will be tallied throughout the day and the school with the most points at the end of the day will be presented with the coveted Headmasters’ Cup. The Buccaneers hope to defend their 2016 victory in capturing the cup over their cross-town rival Tampa Prep. This marks the 14th year of the annual Headmasters’ Challenge.