| Year | Player | School | Player | School |
|---|---|---|---|---|
| 2018 | Freddie Ward | South Fort Myers | Quantavius Brown | Riverdale |
| 2017 | Chris Curry | Lehigh Senior | Cortavius Lee | East Lee |
| 2016 | Darrian Felix | Fort Myers | Zaquandre White | North Ft. Myers |
| 2015 | Willie Johnson | South Fort Myers | Antonio Greaves | Island Coast |
| 2014 | Ryan Watts | Fort Myers | Reshad Washington | Island Coast |
| 2013 | Pierce La Prey | Bishop Verot | Christian Diaz | Island Coast |
| 2012 | Johnell Barnes | Dunbar | Kendall Beck | Riverdale |
| 2011 | Tajarvis Fuller | Dunbar | Steven Mercado | North Ft. Myers |
| 2010 | Chris James | Dunbar | Terrell Davis | East Lee |
| 2009 | Savon Seward | Cypress Lake | Tre Boston | North Ft. Myers |
| 2008 | Antavian Edison | Dunbar | Tommy Bohanon | North Ft. Myers |
| 2007 | Sherman Dyal | South Ft. Myers | West Anderson | Riverdale |
| 2006 | Zachary Brindise | South Ft. Myers | Quenton Washington | North Ft. Myers |
| 2005 | Jeff Banks | Fort Myers | Roberto Perera | North Ft. Myers |
| 2004 | Lionel McGriff | Bishop Verot | Edward Gant | Cape Coral |
| 2003 | Josh Vogelbach | Bishop Verot | Wilford Garner | Dunbar |
| 2002 | Tim Douglas | Fort Myers | Matt Mariana | Estero |
| 2001 | Robert Longoria | Fort Myers | Steve McDonald | Riverdale |
| 2000 | Lemec Bernard | Bishop Verot | Allen Reddick | North Ft. Myers |
| 1999 | Andre McGill | Fort Myers | Tommy Powell | Riverdale |
| 1998 | Chris Vance | Fort Myers | Terrance Chapman | Lehigh |
| 1997 | Finley Carter | Riverdale | Tyrone Davis | Fort Myers |
| 1996 | Chad Terrell | Fort Myers | Kelby Tyre | Cape Coral |
| 1995 | Anthony Henry | Estero | Jamie Thomas | Cape Coral |
| 1994 | Isaac Harvin | Cape Coral | Courtney Nunn | Mariner |
| 1993 | Anthony Dixon | Estero | Kyle Curry | Mariner |
| 1992 | Greg Spires | Mariner | Steve Gary | Cypress Lake |
| 1991 | Rodney Mark | Estero | Joe Crimaldi | Bishop Verot |
| 1990 | Sedrick Watkins | Cypress Lake | Pat Boston | Fort Myers |
| 1989 | Brian Hammermeister | Bishop Verot | Barney Knight | Fort Myers |
Spirit Awards
| Year | Cheerleader | School | Cheerleader | School |
|---|---|---|---|---|
| 2018 | Lauren Turner | Cypress Lake | Erica Paccione | Oasis |
| 2017 | Cierra DeGroot | Fort Myers | Courtney Mitchell | Ida Baker |
| 2015 | Zoe Michael | Fort Myers | Kendall Attwood | Ida Baker |