Cary McDonald Award
|
| 2009-10 | |
| 6A | Winter Park |
| 5A | St. Thomas Aquinas |
| 4A | Lakewood Ranch |
| 3A Private | The Bolles School |
| 3A Public | Baker County |
| 2A Private | Trinity Prep |
| 2A Public | Port St. Joe |
| 1A Private | Oak Hall |
| 1A Public | Altha |
2010-11 |
|
| 8A | Winter Park |
| 7A | St. Thomas Aquinas |
| 6A | Lakewood Ranch |
| 5A | Plantation-American Heritage |
| 4A Private | The Bolles School |
| 4A Public | Tallahassee-Godby |
| 3A Private | Tallahassee-Maclay |
| 3A/2A Public | McKeel Academy |
| 2A Private | All Saints Academy |
| 1A | Union County |
2011-12 |
|
| 8A | Winter Park |
| 7A | St. Thomas Aquinas |
| 6A | Lakewood Ranch |
| 5A | Plantation-American Heritage |
| 4A Private | The Bolles School |
| 4A Public | Godby |
| 3A Private | Tallahassee-Maclay |
| 3A/2A Public | McKeel Academy |
| 2A Private | All Saints Academy |
| 1A | Union County |
2012-13 |
|
| 8A | Cypress Bay/Dr. Phillips |
| 7A | St. Thomas Aquinas |
| 6A | Gainesville |
| 5A | Plantation-American Heritage |
| 4A Private | The Bolles School |
| 4A Public | Madison County |
| 3A Private | Tallahassee-Maclay |
| 3A/2A Public | McKeel Academy |
| 2A Private | All Saints Academy |
| 1A | Lafayette |
2013-14 |
|
| 8A | Winter Park |
| 7A | St. Thomas Aquinas |
| 6A | Creekside |
| 5A | Plantation-American Heritage |
| 4A Private | The Bolles School |
| 4A Public | West Florida |
| 3A Private | Holy Trinity |
| 3A/2A Public | Moore Haven |
| 2A Private | Orlando Christian Prep |
| 1A | Trenton |
2014-15 |
|
| 8A | Cypress Bay |
| 7A | St. Thomas Aquinas |
| 6A | Creekside |
| 5A | Plantation-American Heritage |
| 4A Private | The Bolles School |
| 4A Public | PK Yonge |
| 3A Private | Maclay |
| 3A/2A Public | Moore Haven |
| 2A Private | Academy at the Lakes |
| 1A | Chiefland |
2015-16 |
|
| 8A | Winter Park |
| 7A | St. Thomas Aquinas |
| 6A | Ft.Myers |
| 5A | Plantation-American Heritage |
| 4A Private | The Bolles School |
| 4A Public | Coral Springs Charter |
| 3A Private | Maclay |
| 3A/2A Public | PK Yonge |
| 2A Private | Aucilla Christian |
| 1A | Lafayette |
2016-17 |
|
| 9A | Vero Beach |
| 8A | St. Thomas Aquinas |
| 7A | Ft.Myers |
| 6A | Plantation-American Heritage |
| 5A Private | The Bolles School |
| 5A Public | Florida High |
| 4A Private | Maclay |
| 4A/3A/2A Public | Florida School for Deaf & Blind |
| 3A Private | St. Stephen Episcopal |
| 2A Private | Aucilla Christian |
| 1A | Madison County |
2017-18 |
|
| 9A | Winter Park |
| 8A | St. Thomas Aquinas |
| 7A | Ft.Myers |
| 6A | Plantation-American Heritage |
| 5A Private | The Bolles School |
| 5A Public | Coral Springs Charter |
| 4A Private | Benjamin |
| 4A/3A/2A Public | Marathon |
| 3A Private | Mount Dora Christian |
| 2A Private | Aucilla Christian |
| 1A | Blountstown |
2018-19 |
|
| 9A | Oviedo |
| 8A | St. Thomas Aquinas |
| 7A | Charlotte |
| 6A | Plantation-American Heritage |
| 5A Private | The Bolles School |
| 5A Public | Coral Springs Charter |
| 4A Private | Providence |
| 4A/3A/2A Public | Moore Haven |
| 2A Private | Geneva School |
| 1A | Trenton |
2019-20 |
| 7A | Oviedo |
| 6A | Ponte Vedra |
| 5A | Plantation-American Heritage |
| 4A | Lake Highland Prep |
| 3A | Maclay |
| 2A | The Pine School |
| 1A | Madison County |
2020-21 |
| 7A | Plant |
| 6A | Ponte Vedra |
| 5A | Plantation American Heritage |
| 4A | The Bolles School |
| 3A | First Academy |
| 2A | St Pete Canterbury |
| 1A | Trenton |
2021-22 |
| 7A | Bartram Trail |
| 6A | St. Thomas Aquinas |
| 5A | Bishop Moore |
| 4A | The Bolles School |
| 3A | Berkeley Prep |
| 2A | Cambridge Christian |
| 1A | Madison County |
