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| Year | Kentucky Derby Winner | Jockey | Trainer | Time |
|---|---|---|---|---|
| 2008 | Mine That Bird | Calvin Borel | Bennie L. Woolley, Jr. | 2:02.66 |
| 2008 | Big Brown | Kent Desormeaux | Richard E. Dutrow, Jr. | 2:01.82 |
| 2007 | Street Sense | Calvin Borel | Carl Nafzger | 2:02.17 |
| 2006 | Barbaro | Edgar Prado | Michael R. Matz | 2:01.36 |
| 2005 | Giacomo | Mike E. Smith | John Shirreffs | 2:02.75 |
| 2004 | Smarty Jones | Stewart Elliott | John Servis | 2:04.06 |
| 2003 | Funny Cide | Jose Santos | Barclay Tagg | 2:01.19 |
| 2002 | War Emblem | Victor Espinoza | Bob Baffert | 2:01.13 |
| 2001 | Monarchos | Jorge F. Chavez | John T. Ward, Jr. | 1:59.97 |
| 2000 | Fusaichi Pegasus | Kent Desormeaux | Neil Drysdale | 2:01.00 |
| 1999 | Charismatic | Chris Antley | D. Wayne Lukas | 2:03.20 |
| 1998 | Real Quiet | Kent Desormeaux | Bob Baffert | 2:02.20 |
| 1997 | Silver Charm | Gary Stevens | Bob Baffert | 2:02.40 |
| 1996 | Grindstone | Jerry Bailey | D. Wayne Lukas | 2:01.00 |
| 1995 | Thunder Gulch | Gary Stevens | D. Wayne Lukas | 2:01.20 |
| 1994 | Go for Gin | Chris McCarron | Nick Zito | 2:03.60 |
| 1993 | Sea Hero | Jerry Bailey | Mack Miller | 2:02.40 |
| 1992 | Lil E. Tee | Pat Day | Lynn S. Whiting | 2:03.00 |
| 1991 | Strike the Gold | Chris Antley | Nick Zito | 2:03.00 |
| 1990 | Unbridled | Craig Perret | Carl Nafzger | 2:02.00 |
| 1989 | Sunday Silence | Pat Valenzuela | Charlie Whittingham | 2:05.00 |
| 1988 | Winning Colors | Gary Stevens | D. Wayne Lukas | 2:02.20 |
| 1987 | Alysheba | Chris McCarron | Jack Van Berg | 2:03.40 |
| 1986 | Ferdinand | Bill Shoemaker | Charlie Whittingham | 2:02.80 |
| 1985 | Spend A Buck | Angel Cordero, Jr. | Cam Gambolati | 2:00.20 |
| 1984 | Swale | Laffit Pincay, Jr. | Woody Stephens | 2:02.40 |
| 1983 | Sunny's Halo | Ed Delahoussaye | David C. Cross, Jr. | 2:02.20 |
| 1982 | Gato Del Sol | Ed Delahoussaye | Edwin J. Gregson | 2:02.40 |
| 1981 | Pleasant Colony | Jorge Velasquez | John P. Campo | 2:02.00 |
| 1980 | Genuine Risk | Jacinto Vasquez | LeRoy Jolley | 2:02.00 |
| 1979 | Spectacular Bid | Ronnie Franklin | Bud Delp | 2:02.40 |
| 1978 | Affirmed | Steve Cauthen | Laz Barrera | 2:01.20 |
| 1977 | Seattle Slew | Jean Cruguet | William H. Turner, Jr. | 2:02.20 |
| 1976 | Bold Forbes | Angel Cordero, Jr. | Laz Barrera | 2:01.60 |
| 1975 | Foolish Pleasure | Jacinto Vasquez | LeRoy Jolley | 2:02.00 |
| 1974 | Cannonade | Angel Cordero, Jr. | Woody Stephens | 2:04.00 |
| 1973 | Secretariat | Ron Turcotte | Lucien Laurin | 1:59.40 |
| 1972 | Riva Ridge | Ron Turcotte | Lucien Laurin | 2:01.80 |
| 1971 | Canonero II | Gustavo Avila | Juan Arias | 2:03.20 |
| 1970 | Dust Commander | Mike Manganello | Don Combs | 2:03.40 |
| 1969 | Majestic Prince | Bill Hartack | Johnny Longden | 2:01.80 |
| 1968 | Dancer's Image | Bobby Ussery | Lou Cavalaris, Jr. | 2:02.20 |
| Forward Pass | Ismael Valenzuela | Henry Forrest | ||
| 1967 | Proud Clarion | Bobby Ussery | Loyd Gentry, Jr. | 2:00.60 |
| 1966 | Kauai King | Don Brumfield | Henry Forrest | 2:02.00 |
| 1965 | Lucky Debonair | Bill Shoemaker | Frank Catrone | 2:01.20 |
| 1964 | Northern Dancer | Bill Hartack | Horatio Luro | 2:00.00 |
| 1963 | Chateaugay | Braulio Baeza | James P. Conway | 2:01.80 |
| 1962 | Decidedly | Bill Hartack | Horatio Luro | 2:00.40 |
| 1961 | Carry Back | Johnny Sellers | Jack A. Price | 2:04.00 |
| 1960 | Venetian Way | Bill Hartack | Victor Sovinski | 2:02.40 |
| 1959 | Tomy Lee | Bill Shoemaker | Frank Childs | 2:02.20 |
| 1958 | Tim Tam | Ismael Valenzuela | Jimmy Jones | 2:05.00 |
| 1957 | Iron Liege | Bill Hartack | Jimmy Jones | 2:02.20 |
| 1956 | Needles | David Erb | Hugh L. Fontaine | 2:03.40 |
| 1955 | Swaps | Bill Shoemaker | Mesh Tenney | 2:01.80 |
| 1954 | Determine | Raymond York | Willie Molter | 2:03.00 |
| 1953 | Dark Star | Hank Moreno | Eddie Hayward | 2:02.00 |
| 1952 | Hill Gail | Eddie Arcaro | Ben A. Jones | 2:01.60 |
| 1951 | Count Turf | Conn McCreary | Sol Rutchick | 2:02.60 |
| 1950 | Middleground | William Boland | Max Hirsch | 2:01.60 |
| 1949 | Ponder | Steve Brooks | Ben A. Jones | 2:04.20 |
| 1948 | Citation | Eddie Arcaro | Ben A. Jones | 2:05.40 |
| 1947 | Jet Pilot | Eric Guerin | Tom Smith | 2:06.80 |
| 1946 | Assault | Warren Mehrtens | Max Hirsch | 2:06.60 |
| 1945 | Hoop Jr | Eddie Arcaro | Ivan Parke | 2:07.00 |
| 1944 | Pensive | Conn McCreary | Ben A. Jones | 2:04.20 |
| 1943 | Count Fleet | Johnny Longden | G. Donald Cameron | 2:04.00 |
| 1942 | Shut Out | Wayne Wright | John M. Gaver, Sr. | 2:04.40 |
| 1941 | Whirlaway | Eddie Arcaro | Ben A. Jones | 2:01.40 |
| 1940 | Gallahadion | Carroll Bierman | Roy Waldron | 2:05.00 |
| 1939 | Johnstown | James Stout | Jim Fitzsimmons | 2:03.40 |
| 1938 | Lawrin | Eddie Arcaro | Ben A. Jones | 2:04.80 |
| 1937 | War Admiral | Charley Kurtsinger | George Conway | 2:03.20 |
| 1936 | Bold Venture | Ira Hanford | Max Hirsch | 2:03.60 |
| 1935 | Omaha | Willie Saunders | Jim Fitzsimmons | 2:05.00 |
| 1934 | Cavalcade | Mack Garner | Bob Smith | 2:04.00 |
| 1933 | Brokers Tip | Don Meade | Herbert J. Thompson | 2:06.80 |
| 1932 | Burgoo King | Eugene James | Herbert J. Thompson | 2:05.20 |
| 1931 | Twenty Grand | Charley Kurtsinger | James G. Rowe, Jr. | 2:01.80 |
| 1930 | Gallant Fox | Earl Sande | Jim Fitzsimmons | 2:07.60 |
| 1929 | Clyde Van Dusen | Linus McAtee | Clyde Van Dusen | 2:10.80 |
| 1928 | Reigh Count | Chick Lang | Bert S. Michell | 2:10.40 |
| 1927 | Whiskery | Linus McAtee | Fred Hopkins | 2:06.00 |
| 1926 | Bubbling Over | Albert Johnson | Herbert J. Thompson | 2:03.80 |
| 1925 | Flying Ebony | Earl Sande | William B. Duke | 2:07.60 |
| 1924 | Black Gold | John D. Mooney | Hanley Webb | 2:05.20 |
| 1923 | Zev | Earl Sande | David J. Leary | 2:05.40 |
| 1922 | Morvich | Albert Johnson | Fred Burlew | 2:04.60 |
| 1921 | Behave Yourself | Charles Thompson | Herbert J. Thompson | 2:04.20 |
| 1920 | Paul Jones | Ted Rice | Billy Garth | 2:09.00 |
| 1919 | Sir Barton | Johnny Loftus | H. Guy Bedwell | 2:09.80 |
| 1918 | Exterminator | William Knapp | Henry McDaniel | 2:10.80 |
| 1917 | Omar Khayyam | Charles Borel | Charles T. Patterson | 2:04.60 |
| 1916 | George Smith | Johnny Loftus | Hollie Hughes | 2:04.00 |
| 1915 | Regret | Joe Notter | James G. Rowe, Sr. | 2:05.40 |
| 1914 | Old Rosebud | John McCabe | Frank D. Weir | 2:03.40 |
| 1913 | Donerail | Roscoe Goose | Thomas P. Hayes | 2:04.80 |
| 1912 | Worth | Carroll H. Shilling | Frank M. Taylor | 2:09.40 |
| 1911 | Meridian | George Archibald | Albert Ewing | 2:05.00 |
| 1910 | Donau | Fred Herbert | George Ham | 2:06.40 |
| 1909 | Wintergreen | Vincent Powers | Charles Mack | 2:08.20 |
| 1908 | Stone Street | Arthur Pickens | J. W. Hall | 2:15.20 |
| 1907 | Pink Star | Andy Minder | W. H. Fizer | 2:12.60 |
| 1906 | Sir Huon | Roscoe Troxler | Pete Coyne | 2:08.80 |
| 1905 | Agile | Jack Martin | Robert Tucker | 2:10.75 |
| 1904 | Elwood | Shorty Prior | Charles E. Durnell | 2:08.50 |
| 1903 | Judge Himes | Hal Booker | John P. Mayberry | 2:09.00 |
| 1902 | Alan-a-Dale | Jimmy Winkfield | Tom C. McDowell | 2:08.75 |
| 1901 | His Eminence | Jimmy Winkfield | Frank B. Van Meter | 2:07.75 |
| 1900 | Lieut. Gibson | Jimmy Boland | Charles Hughes | 2:06.25 |
| 1899 | Manuel | Fred Taral | Robert J. Walden | 2:12.00 |
| 1898 | Plaudit | Willie Simms | John E. Madden | 2:09.00 |
| 1897 | Typhoon II | Buttons Garner | J. C. Cahn | 2:12.50 |
| 1896 | Ben Brush | Willie Simms | Hardy Campbell | 2:07.75 |
| 1895 | Halma | Soup Perkins | Byron McClelland | 2:37.50 |
| 1894 | Chant | Frank Goodale | H. Eugene Leigh | 2:41.00 |
| 1893 | Lookout | Eddie Kunze | William McDaniel | 2:39.25 |
| 1892 | Azra | Lonnie Clayton | John Morris | 2:41.50 |
| 1891 | Kingman | Isaac Murphy | Dud Allen | 2:52.25 |
| 1890 | Riley | Isaac Murphy | Edward Corrigan | 2:45.00 |
| 1889 | Spokane | Thomas Kiley | John Rodegap | 2:34.50 |
| 1888 | Macbeth II | George Covington | John Campbell | 2:38.00 |
| 1887 | Montrose | Isaac Lewis | John McGinty | 2:39.25 |
| 1886 | Ben Ali | Paul Duffy | Jim Murphy | 2:36.50 |
| 1885 | Joe Cotton | Babe Henderson | Alex Perry | 2:37.25 |
| 1884 | Buchanan | Isaac Murphy | William Bird | 2:40.25 |
| 1883 | Leonatus | Billy Donohue | Raleigh Colston | 2:43.00 |
| 1882 | Apollo | Babe Hurd | Green B. Morris | 2:40.00 |
| 1881 | Hindoo | Jim McLaughlin | James G. Rowe, Sr. | 2:40.00 |
| 1880 | Fonso | George Lewis | Tice Hutsell | 2:37.50 |
| 1879 | Lord Murphy | Charlie Shauer | George Rice | 2:37.00 |
| 1878 | Day Star | Jimmy Carter | Lee Paul | 2:37.25 |
| 1877 | Baden-Baden | Billy Walker | Edward D. Brown | 2:38.00 |
| 1876 | Vagrant | Bobby Swim | James Williams | 2:38.25 |
| 1875 | Aristides | Oliver Lewis | Ansel Williamson | 2:37.75 |