One of Provincetown's greatest athletic achievements was when the varsity baseball team defeated a much bigger and more talented Mashpee High School team in the 2005 Massachusetts State Playoffs Quarterfinal Round. Provincetown had an enrollment of around 100 students in grades 7–12 at the time, while Mashpee had an enrollment of over 1,000 students. Provincetown defeated Mashpee 7-6 in extra innings and advanced all the way to the Division 3 State Semi-Finals with the victory, the deepest any athletics team at Provincetown had gone in the playoffs in over 15 years.
