The answer is 11. Here are the years: 1986, 1990, 1993, 1995, 1998, 2002, 2004, 2006, 2008, 2009, 2011.

Bolles will be playing for their 12th state championship on December 8th, 2016 against Cocoa. Learn more about that game here – Bolles vs Cocoa state championship game.

Note that not all of these championships have been in 4A football as the divisions have changed in Florida over the years. It is also the case that most high schools change divisions as they grow or as the state grows in terms of high schools.

Here are their other championships:

State Runners-up
1996, 2003, 2012, 2013, 2014

District Champions
1975, 1978, 1979, 1981, 1982, 1983, 1984, 1985, 1986, 1989, 1990, 1991, 1993, 1994, 1995, 1996, 1997, 1998, 1999, 2000, 2001, 2002, 2003, 2004, 2005, 2006, 2007, 2008, 2009, 2010, 2012, 2016