1969
Go Boy’s Black Angel
C. A. Bobo

1970
Ace’s Sensation
Wink Groover

1971
Handshaker’s Delight
Donald Pascal

1972
Ebony’s Black Market
Wink Groover

1973
Super Stock
David Mason

1974
Another Masterpiece
Ronnie Spears

1975
Threat’s Black Power
Billy Gray

1976
The Majority Leader
Wink Groover

1977
Delight’s Cold Ice
Larry Edwards

1978
Delight’s Cold Ice
Larry Edwards

1979
Pride’s Gold Coin
Bill Bobo

1980
The Pusher
Bob McQuerry

1981
CoCo's Sensation
Ronnie Spears

1982
Centennial Delight
Phillip Wilson

1983
Pride's Jubilee Star
Ramsey Bullington

1984
Delight's Counselor
Rae Martin

1985
Delight's Counselor
Rae Martin

1986
Pride's Jubilee Star
Ramsey Bullington

1987
The Secret's Out
Billy Gray

1989
Motown Magic
Steve Dunn

1990
Perfect Cut
Larry Edwards

1991
Wired
Ramsey Bullington

1992
Jubilee's Rising Star
Ramsey Bullington

1993
Ultra Copy
Bill Cantrell

1994
Marker’s Red Mark
Allen McQuerry

1995
Eb’s Cloud Nine
Bill Bobo

1996
Pushers Twist About
Jimmy McConnell

1997
Santana
Jackie McConnell

1998
Generator’s Silver Dollar
Tim Gray

1999
Generator's Champion
Chad Way

2000
Stride’s Touch of Pride
Dick Peebles

2001
Pride's Jubilee Encore
Allan Callaway

2002
Cash's All Star
Larry Edwards

2003
The Whole Nine Yards
Bill Bobo

2004
The Black Night Shade
Jimmy McConnell

2005
Main Power
Joe Cotten

2006
Master Of Jazz
Jimmy McConnell

2007
I'm Packin A Pistol
Jeff Hatcher

2008
Rowdy Rev
Bill Bobo

2009
Golden Sovereign
David Landrum

2010
Sky Miles
Jimmy McConnell

2011
Moody Star
Chad Baucum

2012
Puttin' Cash on the Line
Tim Smith

2013
A Bruce Pearl
Jimmy McConnell

2014
Master's Razzel and Jazz
Herbert Derickson, IV

2015
He's Unleashed
Larry Edwards

2016
A Strong Need for Cash
Michael Wright

2017
Gen' A Mighty
Jimmy McConnell

2018
Reservation Online
Blaise Broccard

2019
The Darkest Honor
Tyler Baucom