| Year | Horse | Trainer | Owner |
| 1939 | Strolling Jim | Floyd Carothers | Col. C. H. Bacon |
| 1940 | Haynes Peacock | Col. J. L. Haynes | Col. J. L. Haynes |
| 1941 | Haynes Peacock | Col. J. L. Haynes | Col. J. L. Haynes |
| 1942 | Melody Maid | Floyd Carothers | Mr. & Mrs. Frank D. Rambo |
| 1943 | Black Angel | Winston Wiser | Mr. & Mrs. R. F. Ellis |
| 1944 | City Girl | Urban Small | M. J. Meyer |
| 1945 | Midnight Sun | Fred Walker | Harlinsdale Farm |
| 1946 | Midnight Sun | Fred Walker | Harlinsdale Farm |
| 1947 | Merry Go Boy | Winston Wiser | Wiser, Mallard, Norman |
| 1948 | Merry Go Boy | Winston Wiser | C. C. Turner |
| 1949 | Midnight Merry | Steve Hill | J. N. McEachern |
| 1950 | Old Glory’s Big Man | Carl Edwards | Mr. & Mrs. J. T. Budd |
| 1951 | The Talk of the Town | Steve Hill | L. A. Chernell & E. P. Ripley |
| 1952 | The Talk of the Town | Steve Hill | L. A. Chernell & E. P. Ripley |
| 1953 | The Talk of the Town | Steve Hill | L. A. Chernell & E. P. Ripley |
| 1954 | White Star | Percy Moss | Dr. W. V. Garnier |
| 1955 | Go Boy’s Shadow | Winston Wiser | Wiser & Padgett |
| 1956 | Go Boy’s Shadow | Winston Wiser | Wiser & Padgett |
| 1957 | Sun’s Jet Parade | Vic Thompson | G. G. Gardebled |
| 1958 | Setting Sun | Sam Paschal | M. M. Bullard |
| 1959 | Rodger’s Perfection | Joe Webb | Dr. Porter Rodgers |
| 1960 | Mack K’s Handshaker | Doug Wolaver | Doug & Myron Wolaver |
| 1961 | B. Major Wilson | Claude Brown | Claude Brown |
| 1962 | Ebony Masterpiece | Sam Paschal | Billy Hale |
| 1963 | Sun’s Delight D | Sam Paschal | Fray Escue |
| 1964 | Perfectionist’s Carbon Copy | Joe Webb | Rodgers, Binns, Raney & Webb |
| 1965 | Triple Threat | Doug Wolaver | Joe Wright |
| 1966 | Shaker’s Shocker | Betty Sain | Betty Sain |
| 1967 | Go Boy’s Sundust | Doug Wolaver | Dr. B. S. Henry |
| 1968 | Go Boy’s Royal Heir | Donald Paschal | Dr. C. L. Sexton |
| 1969 | Ebony’s Senator | Maurice Wilson | O. D. Carlton |
| 1970 | Ace’s Sensation | Wink Groover | Randall Rollins |
| 1971 | Sensational Shadow | C. A. Bobo | Roy & Bonnie Davis |
| 1972 | Handshaker’s Delight A. | Donald Paschal | Dr. C. L. Sexton |
| 1973 | Delight Bumin Around | Billy Gray | John & Mary Miller |
| 1974 | Another Masterpiece | Ronnie Spears | Henry Moore |
| 1975 | Ebony’s True Grit | Joe Fleming | Long Leaf Stables |
| 1976 | Shades of Carbon | Judy Martin | Glen Loe |
| 1977 | The Super Stock | David Mason | Hobart Potter |
| 1978 | Mark of Carbon | Joe Webb | Verdon Walker |
| 1979 | Threat’s Supreme | Bud Seaton | D & S Enterprises |
| 1980 | Ebony’s Mountain Man | Sammy Day | Joe Tillett Jr. |
| 1981 | The Pusher | Bob McQuerry | Joe Dietz family |
| 1982 | Pride’s Secret Threat | Billy Gray | Sand Creek Ranch |
| 1983 | Ebony’s Bold Courier | Joe Fleming | Dr. & Mrs. Roger Bates |
| 1984 | Delight of Pride | Billy Gray | Dr. Andrew Sisk |
| 1985 | Pride’s Final Edition | Ramsey Bullington | Joe Christmas |
| 1986 | Pride’s Jubilee Star | Ramsey Bullington | Bob Parks |
| 1987 | Coin’s Hard Cash | Larry Edwards | Bonnie Cady |
| 1988 | Doc’s High Tribute | Steve Aymett | D. L. Putman |
| 1989 | Motown Magic | Steve Dunn | John Dunn |
| 1990 | The Pushover | Ronnie Spears | Dr. and Mrs. William Varner |
| 1991 | Flashy Pride | Vicki Self | Art & Frances Barnes |
| 1992 | Dark Spirit’s Rebel | Bud Dunn | Shirley & Frank Neal |
| 1993 | The Touch | Chad Way | Hoil & Nancy Walker |
| 1994 | Gen’s Armed and Dangerous | Russ Thompson | Arthur Gordon family |
| 1995 | Pride’s Sundance Star | David Landrum | Dr. & Mrs. Rafael Rigual |
| 1996 | He’s Puttin’ on the Ritz | Sammy Day | William B. & Sandra Johnson |
| 1997 | Generator’s Santana | Jackie McConnell | Kilgore & Castleman |
| 1998 | Masquerading | Knox Blackburn | Gilbert Miller family |
| 1999 | RPM | Bud Dunn | TR & N Partners LLC |
| 2000 | Cash for Keeps | Ray Gilmer | Harrell Browner family |
| 2001 | Pride’s Jubilee Encore | Allan Callaway | Dennis, Pedigo & Terry |
| 2002 | Out On Parole | Steve Dunn | Randall Baskins family |
| 2003 | The Whole Nine Yards | Bill Bobo | Bob & Luanne Sigman family |
| 2004 | The Black Night Shade | Jimmy McConnell | Tom & Judy Waite |
| 2005 | Main Power | Joe Cotten | Holland, King & Kilgore |
| 2007 | Master of Jazz | Jimmy McConnell | Lee Wall & Mike McGartland |
| 2008 | Santana’s El Nino | Link Webb | Michael & Ann Jones |
| 2009 | Watch It Now | Jimmy McConnell | Waterfall Farms |
| 2010 | The Coach | Billy Gray | Holland, Kilgore & Barnes |
| 2011 | Game World | Gary Edwards | Chester & Lynda Stokes |
| 2012 | Walk Time Charlie | Chad Baucom | Holland, Kilgore & Callicutt |
| 2013 | I Am Jose | Casey Wright | Billy & Debbie Woods |
| 2014 | I Am Jose | Casey Wright | Billy & Debbie Woods |
| 2015 | I Am Jose | Casey Wright | Billy & Debbie Woods |
| 2016 | Honors | Larry Edwards | Keith & Dan McSwain |
| 2017 | Gen’s Black Maverick | Bill Callaway | Keith & Lorraine Rosbury |
| 2018 | Gen A Mighty | Jimmy McConnell | Mike Floyd |
| 2019 | I’m Mayhem | Rodney Dick | Jo Ann Dowel |
| 2020 | Master’s Razzle and Jazz | John Allan Callaway | Alan Riddley Family |
| 2021 | Justified Honors | John Allan Callaway | Lisa Baum |
| 2022 | Justified Honors | John Allan Callaway | Lisa Baum |
| 2023 | Justified Honors | John Allan Callaway | Lisa Baum |
| 2024 | Cavender | Tim Smith | Bruce & Robin MacDonald |
| 2025 | Justified Honors | John Allan Callaway | Lisa Baum |
Tennessee Walking Horse National Museum 