Bolles continues to earn recognition as the best in Florida its classification year in and year out, earning an All-Sports award for the 39th year in 2019. Bolles won the Florida High School Athletic Association's Sunshine Cup for the 24th year in 2019, earning the award for 11 consecutive years from 1995-2005 and again from 2007-19. Bolles also claimed the Florida Athletic Coaches Association's Carey E. McDonald All-Sports Award for 39 years, beginning in 1980.
Bolles has also been recognized nationally by several organizations. 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. That year, the Jacksonville City Council presented a resolution commending Bolles' athletic success. 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.