The internationally recognized athletic program at Bolles provides students in middle and upper school the opportunity to learn, grow, and develop into well-rounded individuals. Participation and camaraderie are as important as competition and success in the overall educational aspect of the athletic program. While Bolles teams and athletes are often recognized for outstanding achievements and results on the field, the important lessons of leadership, self-discipline, and teamwork are the lasting rewards possible through athletic involvement at the School.
With 61 teams at the middle, junior varsity, and varsity levels, Bolles offers a full complement of athletic opportunities. The student body regularly approaches or exceeds 90% participation in one or more sports.
Athletic opportunities for middle school students include middle school only teams in some sports and participation with upper school teams in some sports, where appropriate. Many of the middle school teams compete within the Independent Middle School Conference with other area private middle school level teams.
Notable achievements include:
- The Bolles School athletic program has been recognized by several organizations as one of the best in the nation. In 2009, ESPN RISE ranked Bolles as the #1 boys' athletic program in the country and MaxPreps named Bolles the third best overall athletic program nationally in the same year. In 2005, Sports Illustrated ranked Bolles as the ninth best athletic program out of 38,000 high schools in the nation over the previous 10 years.
- In Florida, Bolles continues to earn recognition as the best in its classification year in and year out, earning an All-Sports award for the 36th year in 2016. Bolles won the Florida High School Athletic Association's Sunshine Cup for the 21st year in 2016, earning the award for 11 consecutive years from 1995-2005 and again from 2007-16. Bolles also claimed the Florida Athletic Coaches Association's Carey E. McDonald All-Sports Award for 36 years, beginning in 1980.
- Bolles teams have won a total of 123 team state titles with 84 state runner-up finished in 17 different sports.
- Bolles teams have ranked among the best in the nation highlighted by nine national titles and a national runner-up finish in girls' swimming and eight national titles and national runner-up finishes in boys' swimming
- Bolles football coach Corky Rogers holds the most state titles (10) and wins (454 through the 2015 season) among high school football coaches in Florida history.
- The middle school athletics program has claimed 36 Independent Middle School Conference championships since Bolles joined the conference in 2007.