| June 14, 1953 | Five Flags Speedway, Pensacola, FL | NASCAR Grand National | Herb Thomas | |
| February 17, 1957 | Five Flags Speedway, Pensacola, FL | USAC Tangerine Tournament Midget | Jimmy Knight | |
| July 5, 1981 | Five Flags Speedway, Pensacola, FL | NASCAR Grand American | Ronnie Sanders | |
| September 6, 1981 | Five Flags Speedway, Pensacola, FL | NASCAR Grand American | Ronnie Sanders | |
| December 5, 1982 | Snowball Derby | Five Flags Speedway, Pensacola, FL | NASCAR Grand American | Gene Morgan |
| July 15, 1983 | Five Flags Speedway, Pensacola, FL | All Pro Stock Car | Rusty Wallace | |
| September 17, 1983 | Five Flags Speedway, Pensacola, FL | All Pro Stock Car | Jody Ridley | |
| March 25, 1984 | Five Flags Speedway, Pensacola, FL | All Pro Stock Car | Rusty Wallace | |
| September 29, 1984 | Five Flags Speedway, Pensacola, FL | All Pro Stock Car | Freddy Fryar | |
| December 9, 1984 | Snowball Derby | Five Flags Speedway, Pensacola, FL | All Pro Stock Car | Butch Lindley |
| March 10, 1985 | Neil Bonnett Race Cars 200 | Five Flags Speedway, Pensacola, FL | All Pro Stock Car | Butch Lindley |
| July 12, 1985 | Auto Parts Spectacular 200 | Five Flags Speedway, Pensacola, FL | All Pro Stock Car | Freddy Fryar |
| September 28, 1985 | Bolaws 200 | Five Flags Speedway, Pensacola, FL | All Pro Stock Car | Freddy Fryar |
| December 8, 1985 | Snowball Derby | Five Flags Speedway, Pensacola, FL | All Pro Stock Car | Jody Ridley |
| March 23, 1986 | Neil Bonnett Race Cars 250 | Five Flags Speedway, Pensacola, FL | All Pro Stock Car | Jody Ridley |
| June 20, 1986 | Pensacola 200 | Five Flags Speedway, Pensacola, FL | All Pro Stock Car | Rusty Wallace |
| August 1, 1986 | Moroso Twin 150 | Five Flags Speedway, Pensacola, FL | All Pro Stock Car | Rusty Wallace |
| September 27, 1986 | Cam2 100 | Five Flags Speedway, Pensacola, FL | All Pro KISS | Mike Oliver |
| October 26, 1986 | Longcut 200 | Five Flags Speedway, Pensacola, FL | All Pro Stock Car | Steve Grissom |
| December 7, 1986 | Snowball Derby | Five Flags Speedway, Pensacola, FL | All Pro Stock Car | Gary Balough |
| March 8, 1992 | Southern 300 | Five Flags Speedway, Pensacola, FL | ARCA Stock Car | Roy Payne |
| March 7, 1993 | Southern 300 | Five Flags Speedway, Pensacola, FL | ARCA Stock Car | Harold Fair |
| July 30, 1993 | Winston Doubleheader 200 | Five Flags Speedway, Pensacola, FL | NASCAR All Pro Series | Bobby Gill |
| May 6, 1994 | Southern 200 | Five Flags Speedway, Pensacola, FL | ARCA Stock Car | Gary Bradberry |
| May 5, 1995 | Southern 200 | Five Flags Speedway, Pensacola, FL | ARCA Stock Car | Bob Schacht |
| May 4, 1996 | Southern 200 | Five Flags Speedway, Pensacola, FL | ARCA Stock Car | Frank Kimmel |
| May 4, 1997 | Florida 300 | Five Flags Speedway, Pensacola, FL | ASA Stock Car | Mike Garvey |
| March 31, 2001 | Lucas Oil 250 | Five Flags Speedway, Pensacola, FL | USAR Pro Cup Southern | Bobby Gill |
| March 16, 2002 | Naturally Fresh Foods 250 | Five Flags Speedway, Pensacola, FL | USAR Pro Cup Southern | Bobby Gill |
| May 5, 2002 | ASARacing.com 300 | Five Flags Speedway, Pensacola, FL | ASA Stock Car | Joey Clanton |
| April 13, 2012 | Southern Shootout | Five Flags Speedway, Pensacola, FL | Must See Racing Sprint Car | Tanner Swanson |
| December 1, 2012 | Snowflake 100 | Five Flags Speedway, Pensacola, FL | Pro Late Model | Chase Elliott |
| December 2, 2012 | 45th Snowball Derby | Five Flags Speedway, Pensacola, FL | Super Late Model | Erik Jones |
| March 22, 2013 | Southern Shootout | Five Flags Speedway, Pensacola, FL | Must See Racing Sprint Car | Ryan Litt |
| April 13, 2013 | NAPA Auto Parts 150 | Five Flags Speedway, Pensacola, FL | NASCAR East Series | Ben Kennedy |
| April 11, 2014 | Southern Shootout | Five Flags Speedway, Pensacola, FL | Must See Racing Sprint Car | Aaron Pierce |
| June 13, 2014 | Pensacola 150 | Five Flags Speedway, Pensacola, FL | NASCAR East Series | Ben Rhodes |
| April 17, 2015 | King of the Wing | Five Flags Speedway, Pensacola, FL | USAC AVSS Sprint Car | Bobby Santos III |
| March 9, 2019 | Pensacola 200 | Five Flags Speedway, Pensacola, FL | ARCA Stock Car | Michael Self |
| October 11, 2020 | Pensacola 200 | Five Flags Speedway, Pensacola, FL | ARCA East Series | Sam Mayer |
| February 27, 2021 | Pensacola 200 | Five Flags Speedway, Pensacola, FL | ARCA East Series | Sammy Smith |
| March 19, 2022 | Pensacola 200 | Five Flags Speedway, Pensacola, FL | ARCA East Series | Sammy Smith |
| June 18, 2022 | Five Flags Speedway, Pensacola, FL | SRX Stock Car | Hélio Alves de Castroneves | |
| March 25, 2023 | Pensacola 200 | Five Flags Speedway, Pensacola, FL | ARCA East Series | William Sawalich |
| March 24, 2024 | Pensacola 150 | Five Flags Speedway, Pensacola, FL | ARCA East Series | Giovanni Ruggiero |