| 1893 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Oro Wilkes US-30347
| John A. Goldsmith | | | |
| 1894 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Beuzetta
| Gus Macey | | | |
| 1895 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Oakland Baron US-31586
| W.W. Milam | | | |
| 1896 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Rose Croix
| Myron E. McHenry | | | |
| 1897 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Thorn
| Orin A. Hickok | | | |
| 1898 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Peter The Great US-28955
| P.V. Johnson | | | |
| 1899 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Boralma
| Gus Macey | | | |
| 1900 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Ferreno
| Ed Benyon | | | |
| 1901 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Peter Stirling
| J.B. Chandler | | | |
| 1902 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Nella Jay
| F.D. McKey | | | |
| 1903 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Sadie Mac
| A. McDonald | | | |
| 1904 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Grace Bond
| W.J. Andrews | | | |
| 1905 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Miss Adbell
| A. McDonald | | | |
| 1906 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Siliko US-40903
| McHenry / W. McCart | | | |
| 1907 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | General Watts US-44231
| M. Bowerman | | | |
| 1908 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | The Harvester US-43637
| Pop Geers | | | |
| 1909 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Baroness Virginia
| Thomas W. Murphy | | | |
| 1910 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Grace Shaw
| M.C. McDewitt | | | |
| 1911 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Peter Thompson
| Jos. L. Serrill | | | |
| 1912 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Manrico B US-58288
| W.G. Durfee | | | |
| 1913 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Etawah US-57715
| Pop Geers | | | |
| 1914 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Peter Volo US-57574
| Thomas W. Murphy | | | |
| 1915 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Mary Putney
| R.D. McMahon | | | |
| 1916 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Volga E.
| Ben White | | | |
| 1917 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | The Real Lady
| Thomas W. Murphy | | | |
| 1918 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Nella Dillon
| Jos L. Serrill | | | |
| 1919 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Periscope
| J.L. Dodge | | | |
| 1920 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Arion Guy US-65042
| Harry Stokes | | | |
| 1921 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Rose Scott
| Thomas W. Murphy | | | |
| 1922 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Lee Worthy US-66075
| Ben White | | | |
| 1923 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Ethelinda
| Walter Cox | | | |
| 1924 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Mr McElwyn US-68461
| Ben White | | | |
| 1925 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Aileen Guy
| Ben White | | | |
| 1926 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Guy McKinney US-67486
| Nat Ray | | | |
| 1927 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Iosola's Worthy
| Marvin Childs | | | |
| 1928 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Spencer US-68128
| W.H. Leese | | | |
| 1929 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Walter Dear US-69581
| Walter Cox | | | |
| 1930 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Hanover's Bertha
| Tom Berry | | | |
| 1931 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Protector US-69365
| William Caton | | | |
| 1932 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | The Marchioness
| William Caton | | | |
| 1933 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Meda US-303906
| Ben White | | | |
| 1934 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Princess Peg
| Sep Palin | | | |
| 1935 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Lawrence Hanover US-71090
| Henry Thomas | | | |
| 1936 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Rosalind
| Ben White | | | |
| 1937 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Twilight Song
| Ben White | | | |
| 1938 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | McLin Hanover US-72415
| Henry Thomas | | | |
| 1939 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Peter Astra US-72222
| Doc Parshall | | | |
| 1940 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Spencer Scott US-72444
| Fred Egan | | | |
| 1941 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Bill Gallon US-73350
| Lee Smith | | | |
| 1942 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | | | | | |
| 1943 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | | | | | |
| 1944 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | | | | | |
| 1945 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | | | | | |
| 1946 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Victory Song US-76207
| Sep Palin | | | |
| 1947 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Hoot Mon US-76700
| Sep Palin | | | |
| 1948 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Egan Hanover US-77749
| Ralph Baldwin | | | |
| 1949 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Bangaway US-78636
| Ralph Baldwin | | | |
| 1950 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Star's Pride US-80141
| Harry Pownall Sr | | | |
| 1951 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Ford Hanover US-81215
| John Simpson Sr | | | |
| 1952 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Sharp Note US-82961
| Bion Shively | | | |
| 1953 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Kimberly Kid US-84638
| Thomas Berry | | | |
| 1954 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Harlan US-89206
| Delvin Miller | | | |
| 1955 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Scott Frost US-88887
| Joe O'Brien | | | |
| 1956 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Nimble Colby
| Ralph Baldwin | | | |
| 1957 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Cassin Hanover
| Fred Egan | | | |
| 1958 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Emily's Pride
| Flave Nipe | | | |
| 1959 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Diller Hanover US-97806
| Ralph Baldwin | | | |
| 1960 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Elaine Rodney
| Clint Hodgins | | | |
| 1961 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Duke Rodney US-102475
| Eddie Wheeler | | | |
| 1962 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Safe Mission US-67256
| Joe O'Brien | | | |
| 1963 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Speedy Scot US-108446
| Ralph Baldwin | | | |
| 1964 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Ayres US-3144-A
| John Simpson Jr | | | |
| 1965 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Armbro Flight US-3129-B
| Joe O'Brien | | | |
| 1966 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Governor Armbro US-2458-C
| Joe O'Brien | | | |
| 1967 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Speed Model US-2008-D
| Art Hult | | | |
| 1968 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Nevele Pride US-7308-E
| Stanley Dancer | | | |
| 1969 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Lindy's Pride US-2554-F
| Howard Beissinger | | | |
| 1970 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Timothy T US-6613-G
| John Simpson Jr | | | |
| 1971 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Savoir US-2021-H
| James Arthur | | | |
| 1972 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Super Bowl US-8540-I
| Stanley Dancer | | | |
| 1973 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Arnie Almahurst US-5717-J
| Joe O'Brien | | | |
| 1974 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Waymaker US-6551-K
| John Simpson Jr | | | |
| 1975 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Noble Rogue US-1234-L
| Billy Herman | | | |
| 1976 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Quick Pay US-4781-P
| Peter Haughton | | | |
| 1977 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Texas US-6915-R
| Billy Herman | | | |
| 1978 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Doublemint US-066-AS
| Peter Haughton | | | |
| 1979 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Classical Way US-3108-T
| John Simpson Jr | | | |
| 1980 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Final Score US-7957-V
| Tom Haughton | | | |
| 1981 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Filet Of Sole US-761-CW
| John Simpson Jr | | | |
| 1982 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Jazz Cosmos US-396-AX
| Mickey McNichol | | | |
| 1983 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Power Seat US-0631-Y
| Bill O'Donnell | | | |
| 1984 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Fancy Crown US-916-CZ
| Bill O'Donnell | | | |
| 1985 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Flak Bait US-A-4236
| Ben Webster | | | |
| 1986 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Sugarcane Hanover US-588-BB
| Ron Waples | | | |
| 1987 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Napoletano US-C-5382
| Bill O'Donnell | | | |
| 1988 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Huggie Hanover US-D-8690
| Ron Waples | | | |
| 1989 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Peace Corps US-6255-E
| John Campbell | | | |
| 1990 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Star Mystic US-F-4715
| Jan Johnson | | | |
| 1991 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Whiteland Janice US-GC-839
| Michel Lachance | | | |
| 1992 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Armbro Keepsake C-HY-560
| John Campbell | | | |
| 1993 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Pine Chip US-J-8637
| John Campbell | | | |
| 1994 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Bullville Victory US-1233-K
| John Campbell | | | |
| 1995 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | CR Track Master US-L-7993
| Mike Allen | | | |
| 1996 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Running Sea US-0054-M
| Wally Hennessey | | | |
| 1997 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Take Chances US-N-6133
| Wally Hennessey | | | |
| 1998 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Trade Balance US-P-5259
| David Wade | | | |
| 1999 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Self Possessed US-R-6740
| Michel Lachance | | | |
| 2000 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Credit Winner US-SC-783
| Jim Meittinis | | | |
| 2001 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Chasing Tail US-TG-571
| John Campbell | | | |
| 2002 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Like A Prayer US-V-2784
| Ron Pierce | | | |
| 2003 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Mr Muscleman US-WA-977
| Ron Pierce | | | |
| 2004 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Windsong's Legacy US-X-9971
| Trond Smedshammer | | | |
| 2005 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Strong Yankee US-Z-7663
| Brian Sears | | | |
| 2006 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Glidemaster US-1AF-97
| John Campbell | | | |
| 2007 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Donato Hanover US-2BE-08
| Ron Pierce | | | |
| 2008 | The Red Mile Racetrack, Lexington, Kentucky | Deweycheatumnhowe US-0CA-03
| Ray Schnittker | 14,3a | 252 280 USD | 1 kpl |
| 2009 | The Red Mile Racetrack, Lexington, Kentucky, Yhdysvallat | Muscle Hill US-3D-568
| Brian Sears | | | |
| 2010 | The Red Mile, Lexington, Kentucky | Wishing Stone US-6E-472
| George Brennan | | | |
| 2011 | The Red Mile, Lexington, Kentucky | Manofmanymissions US-1F-333
| David Miller | | | |
| 2012 | The Red Mile, Lexington, Kentucky | My MVP US-3G-722
| Mike Lachance | | | |
| 2013 | The Red Mile, Lexington, Kentucky | Creatine US-8HA-47
| Mike Lachance | | | |
| 2014 | The Red Mile, Lexington, Kentucky | Nuncio US-8J-260
| John Campbell | 09,4a | 217 500 USD | |
| 2015 | The Red Mile, Lexington, Kentucky | Pinkman US-6K-358
| Yannick Gingras | 09,2a | 263 500 USD | |
| 2016 | The Red Mile, Lexington, Kentucky | Marion Marauder US-0L-145
| Scott Zeron | 10,0a | 215 500 USD | |
| 2017 | The Red Mile, Lexington, Kentucky | Snowstorm Hanover US-0M-819
| Matt Kakaley | 10,5a | 210 000 USD | 1 kpl |
| 2018 | The Red Mile, Lexington, Kentucky | Six Pack US-7N-714
| Åke Svanstedt | 07,9a ME | 217 000 USD | 3 kpl |
| 2019 | The Red Mile, Lexington, Kentucky | Greenshoe US-8P-217
| Brian Sears | 09,1a | 225 000 USD | |
| 2020 | The Red Mile, Lexington, Kentucky | Amigo Volo US-2R-592
| Dexter Dunn | 09,0a | 222 000 USD | |
| 2021 | The Red Mile, Lexington, Kentucky | Jujubee US-1S-505
| Andrew McCarthy | 08,1a | 280 500 USD | |
| 2022 | The Red Mile, Lexington, Kentucky | Rebuff US-8T-880
| Tim Tetrick | 08,7a | 215 000 USD | |
| 2023 | The Red Mile, Lexington, Kentucky | Tactical Approach US-2V-193
| Scott Zeron | 09,6a | 225 000 USD | |
| 2024 | The Red Mile, Lexington, Kentucky | Sig Sauer US-6WB-57
| Andrew McCarthy | 08,1a | 250 000 USD | |
