| Year | Winner | Jockey | Trainer | Sire | Time** |
|---|---|---|---|---|---|
| 2009 | ??? | ??? | ??? | ??? | ??? |
| 2008 | Big Brown | Kent Desormeaux | Rick Dutrow | Boundary | 2:01.82 |
| 2007 | Street Sense | Calvin Borel | Carl Nafzger | Street Cry | 2:02.17 |
| 2006 | Barbaro | Edgar Prado | Michael Matz | Dynaformer | 2:01.36 |
| 2005 | Giacomo | Mike Smith | John Shirreffs | Holy Bull | 2:02.75 |
| 2004 | Smarty Jones | Stewart Elliott | John Servis | Elusive Quality | 2:04.06 |
| 2003 | Funny Cide | Jose Santos | Barclay Tagg | Distorted Humor | 2:01.19 |
| 2002 | War Emblem | Victor Espinoza | Bob Baffert | Our Emblem | 2:01.13 |
| 2001 | Monarchos | Jorge Chavez | John Ward | Maria's Mon | 1:59.97 |
| 2000 | Fusaichi Pegasus | Kent Desormeaux | Neil Drysdale | Mr. Prospector | 2:01.12 |
| 1999 | Charismatic | Chris Antley | D. Wayne Lukas | Summer Squall | 2:03.29 |
| 1998 | Real Quiet | Kent Desormeaux | Bob Baffert | Quiet American | 2:02 2/5 |
| 1997 | Silver Charm | Gary Stevens | Bob Baffert | Silver Buck | 2:02 2/5 |
| 1996 | Grindstone | Jerry Bailey | D. Wayne Lukas | Unbridled | 2:02 |
| 1995 | Thunder Gulch | Gary Stevens | D. Wayne Lukas | Gulch | 2:01 1/5 |
| 1994 | Go For Gin | Chris McCarron | Nick Zito | Cormorant | 2:03 3/5 |
| 1993 | Sea Hero | Jerry Bailey | MacKenzie Miller | Polish Navy | 2:02 2/5 |
| 1992 | Lil E. Tee | Pat Day | Lynn Whiting | At The Threshold | 2:03 |
| 1991 | Strike The Gold | Chris Antley | Nick Zito | Alydar | 2:03 |
| 1990 | Unbridled | Craig Perret | Carl Nafzger | Fappiano | 2:02 |
| 1989 | Sunday Silence | Pat Valenzuela | Charlie Whittingham | Halo | 2:05 |
| 1988 | Winning Colors(f) | Gary Stevens | D. Wayne Lukas | Caro | 2:02 1/5 |
| 1987 | Alysheba | Chris McCarron | Jack Van Berg | Alydar | 2:03 2/5 |
| 1986 | Ferdinand | Willie Shoemaker | Charlie Whittingham | Nijinsky II | 2:02 4/5 |
| 1985 | Spend A Buck | Angel Cordero, Jr. | Cam Gambolati | Buckaroo | 2:00 1/5 |
| 1984 | Swale | Lafit Pincay, Jr. | Woody C. Stephens | Seattle Slew | 2:02 2/5 |
| 1983 | Sunny's Halo | Eddie Delahoussaye | David C. Cross Jr. | Halo | 2:02 1/5 |
| 1982 | Gato Del Sol | Eddie Delahoussaye | Edwin Gregson | Cougar II | 2:02 2/5 |
| 1981 | Pleasant Colony | Jorge Velasquez | John Campo | His Majesty | 2:02 |
| 1980 | Genuine Risk(f) | Jacinto Vasquez | LeRoy Jolley | Exclusive Native | 2:02 |
| 1979 | Spectacular Bid | Ron Franklin | Grover G. (Bud) Delp | Bold Bidder | 2:02 2/5 |
| 1978 | Affirmed(TC) | Steve Cauthen | Laz Barrera | Exclusive Native | 2:01 1/5 |
| 1977 | Seattle Slew(TC) | Jean Cruguet | William H. Turner Jr. | Bold Reasoning | 2:02 1/5 |
| 1976 | Bold Forbes | Angel Cordero, Jr. | Laz Barrera | Irish Castle | 2:01 3/5 |
| 1975 | Foolish Pleasure | Jacinto Vasquez | LeRoy Jolley | What A Pleasure | 2:02 |
| 1974 | Cannonade | Angel Cordero Jr. | Woody C. Stephens | Bold Bidder | 2:04 |
| 1973 | Secretariat(TC) | Ron Turcotte | Lucien Laurin | Bold Ruler | 1:59 2/5*** |
| 1972 | Riva Ridge | Ron Turcotte | Lucien Laurin | First Landing | 2:01 4/5 |
| 1971 | Canonero II | Gustavo Avila | Juan Arias | Pretendre | 2:03 1/5 |
| 1970 | Dust Commander | Mike Manganello | Don Combs | Bold Commander | 2:03 2/5 |
| 1969 | Majestic Prince | Bill Hartack | John Longden | Raise A Native | 2:01 4/5 |
| 1968 | Forward Pass* | Ismael Valenzuela | Henry Forrest | On-and-On | 2:02 1/5 |
| 1967 | Proud Clarion | Bobby Ussery | Loyd Gentry | Hail to Reason | 2:00 3/5 |
| 1966 | Kauai King | Don Brumfield | Henry Forrest | Native Dancer | 2:02 |
| 1965 | Lucky Debonair | Willie Shoemaker | Frank Calrone | Vertex | 2:01 1/5 |
| 1964 | Northern Dancer | Bill Hartack | Horatio A. Luro | Nearctic | 2:00 |
| 1963 | Chateaugay | Braulio Baeza | Jimmy P. Conway | Swaps | 2:01 4/5 |
| 1962 | Decidedly | Bill Hartack | Horatio A. Luro | Determine | 2:00 2/5 |
| 1961 | Carry Back | John Sellers | Jack A. Price | Saggy | 2:04 |
| 1960 | Venetian Way | Bill Hartack | Vic J. Sovinski | Royal Coinage | 2:02 2/5 |
| 1959 | Tomy Lee | Willie Shoemaker | Frank Childs | Tudor Minstrel | 2:02 1/5 |
| 1958 | Tim Tam | Ismael Valenzuela | H.A. Jones | Tom Fool | 2:05 |
| 1957 | Iron Liege | Bill Hartack | H.A. Jones | Bull Lea | 2:02 1/5 |
| 1956 | Needles | David Erb | Hugh L. Fontaine | Ponder | 2:03 2/5 |
| 1955 | Swaps | Willie Shoemaker | Mesh A. Tenney | Khaled | 2:01 4/5 |
| 1954 | Determine | Raymond York | Willie Molter | Alibhai | 2:03 |
| 1953 | Dark Star | Hank Moreno | Eddie Hayward | Royal Gem II | 2:02 |
| 1952 | Hill Gail | Eddie Arcaro | Ben A. Jones | Bull Lea | 2:01 3/5 |
| 1951 | Count Turf | Conn McCreary | Sol Rutchick | Count Fleet | 2:02 3/5 |
| 1950 | Middleground | Willie Boland | Max Hirsch | Bold Venture | 2:01 3/5 |
| 1949 | Ponder | Steve Brooks | Ben A. Jones | Pensive | 2:04 1/5 |
| 1948 | Citation(TC) | Eddie Arcaro | Ben A. Jones | Bull Lea | 2:05 2/5 |
| 1947 | Jet Pilot | Eric Guerin | Tom Smith | Blenheim II | 2:06 4/5 |
| 1946 | Assault(TC) | Warren Mehrtens | Max Hirsch | Bold Venture | 2:06 3/5 |
| 1945 | Hoop Jr. | Eddie Arcaro | Ivan H. Parke | Sir Gallahad III | 2:07 |
| 1944 | Pensive | Conn McCreary | Ben A. Jones | Hyperion | 2:04 1/5 |
| 1943 | Count Fleet(TC) | Johnny Longden | G. Don Cameron | Reigh Count | 2:04 |
| 1942 | Shut Out | Wayne Wright | John M. Gaver | Equipoise | 2:04 2/5 |
| 1941 | Whirlaway(TC) | Eddie Arcaro | Ben A. Jones | Blenheim II | 2:01 2/5 |
| 1940 | Gallahadion | Carroll Bierman | Roy Waldron | Sir Gallahad III | 2:05 |
| 1939 | Johnstown | Jimmy Stout | James Fitzsimmons | Jamestown | 2:03 2/5 |
| 1938 | Lawrin | Eddie Arcaro | Ben A. Jones | Insco | 2:04 2/5 |
| 1937 | War Admiral(TC) | Charles Kurtsinger | George Conway | Man o' War | 2:03 1/5 |
| 1936 | Bold Venture | Ira Handford | Max Hirsch | St. Germans | 2:03 3/5 |
| 1935 | Omaha(TC) | Willie Saunders | James Fitzsimmons | Gallant Fox | 2:05 |
| 1934 | Cavalcade | Mack Garner | Robert A. Smith | Lancegaye | 2:04 |
| 1933 | Brokers Tip | Don Meade | H.J. Thompson | Black Toney | 2:06 4/5 |
| 1932 | Burgoo King | Eugene James | H.J. Thompson | Bubbling Over | 2:05 1/5 |
| 1931 | Twenty Grand | Charles Kurtsinger | James Rowe Jr. | St. Germans | 2:01 4/5 |
| 1930 | Gallant Fox(TC) | Earl Sande | James Fitzsimmons | Sir Gallahadion | 2:07 3/5 |
| 1929 | Clyde Van Dusen | Linus McAtee | Clyde Van Dusen | Man o' War | 2:10 4/5 |
| 1928 | Reigh Count | Chick Lang | Bert S. Michell | Sunreigh | 2:10 2/5 |
| 1927 | Whiskery | Linus McAtee | Fred Hopkins | Whisk Broom II | 2:06 |
| 1926 | Bubbling Over | Albert Johnson | H.J. Thompson | North Star III | 2:04 3/5 |
| 1925 | Flying Ebony | Earl Sande | William B. Duke | The Finn | 2:07 3/5 |
| 1924 | Black Gold | J.D. Mooney | Hanly Webb | Black Toney | 2:05 1/5 |
| 1923 | Zev | No | D.J. Leary | The Finn | 2:05 2/5 |
| 1922 | Morvich | Albert Johnson | Fred Burlew | Runnymede | 2:04 3/5 |
| 1921 | Behave Yourself | Charles Thompson | H.J. Thompson | Marathon | 2:04 1/5 |
| 1920 | Paul Jones | Ted Rice | William Garth | Sea King | 2:09 |
| 1919 | Sir Barton(TC) | Johnny Loftus | H. Guy Bedwell | Star Shoot | 2:09 4/5 |
| 1918 | Exterminator | Willie Knapp | Henry McDaniel | McGee | 2:10 4/5 |
| 1917 | Omar Khayyam | Charles Borel | C.T. Patterson | Marco | 2:04 3/5 |
| 1916 | George Smith | Johnny Loftus | Hollie Hughes | Out of Reach | 2:04 |
| 1915 | Regret(f) | Joe Notter | James Rowe Sr. | Broomstick | 2:05 2/5 |
| 1914 | Old Rosebud | John McCabe | Frank D. Weir | Uncle | 2:03 2/5 |
| 1913 | Donerail | Roscoe Goose | T.P. Hayes | McGee | 2:04 4/5 |
| 1912 | Worth | Carroll H. Shilling | Frank M. Taylor | Knight of the Thistle | 2:09 2/5 |
| 1911 | Meridian | George Archibald | Albert Ewing | Broomstick | 2:05 |
| 1910 | Donau | Fred Herbert | George Ham | Woolsthorpe | 2:06 2/5 |
| 1909 | Wintergreen | Vincent Powers | Charles Mack | Dick Welles | 2:08 1/5 |
| 1908 | Stone Street | Arthur Pickens | John W. Hall | Longstreet | 2:15 1/5 |
| 1907 | Pink Star | Andy Minder | W.H. Fizer | Pink Coat | 2:12 3/5 |
| 1906 | Sir Huon | Roscoe Troxler | Peter Coyne | Falsetto | 2:08 4/5 |
| 1905 | Agile | Jack Martin | Robert Tucker | Sir Dixon | 2:10 3/4 |
| 1904 | Elwood | Shorty Prior | Charles E. Durnell | Free Knight | 2:08 1/2 |
| 1903 | Judge Himes | Hal Booker | J.P. Mayberry | Esher | 2:09 |
| 1902 | Alan-A-Dale | Jimmy Winkfield | Thomas C. McDowell | Halma | 2:08 3/4 |
| 1901 | His Eminence | Jimmy Winkfield | Frank B. Van Meter | Falsetto | 2:07 3/4 |
| 1900 | Lieut. Gibson | Jimmy Boland | Charles H. Hughes | G.W. Johnson | 2:06 1/4 |
| 1899 | Manuel | Fred Taral | Robert J. Walden | Bob Miles | 2:12 |
| 1898 | Plaudit | Willie Simms | John E. Madden | Himyar | 2:09 |
| 1897 | Typhoon II | Buttons Garner | J.C. Cahn | Top Gallant | 2:12 1/2 |
| 1896 | Ben Brush | Willie Simms | Hardy Campbell | Bramble | 2:07 3/4 |
| 1895 | Halma | Soup Perkins | Byron McClelland | Hanover | 2:37 1/2 |
| 1894 | Chant | Frank Goodale | Eugene Leigh | Falsetto | 2:41 |
| 1893 | Lookout | Eddie Kunze | William McDaniel | Troubador | 2:39 1/4 |
| 1892 | Azra | Lonnie Clayton | John H. Morris | Reform | 2:41 1/2 |
| 1891 | Kingman | Isaac Murphy | Dud Allen | Glengarry | 2:52 1/2 |
| 1890 | Riley | Isaac Murphy | Edward Corrigan | Longfellow | 2:45 |
| 1889 | Spokane | Thomas Kiley | John Rodegap | Hyder Ali | 2:34 1/2 |
| 1888 | Macbeth II | George Covington | John Campbell | Macduff | 2:38 1/4 |
| 1887 | Montrose | Isaac Lewis | John McGinly | Duke of Montrose | 2:39 1/4 |
| 1886 | Ben Ali | Paul Duffy | Jim Murphy | Virgil | 2:36 1/2 |
| 1885 | Joe Cotton | Babe Henderson | Alex Perry | King Alfonso | 2:37 1/4 |
| 1884 | Buchanan | Isaac Murphy | William Bird | Buckden | 2:40 1/4 |
| 1883 | Leonatus | Billie Donohue | John McGinty | Longfellow | 2:43 |
| 1882 | Apollo | Babe Hurd | Green B. Morris | Ashtead or Lever | 2:40 1/4 |
| 1881 | Hindoo | Jim McLaughlin | James Rowe Sr. | Virgil | 2:40 |
| 1880 | Fonso | George Lewis | Tice Hutsell | King Alfonso | 2:37 1/2 |
| 1879 | Lord Murphy | Charles Shauer | George Rice | Pat Malloy | 2:37 |
| 1878 | Day Star | Jimmy Carter | Lee Paul | Star Davis | 2:37 1/4 |
| 1877 | Baden-Baden | Billie Walker | Ed Brown | Australian | 2:38 |
| 1876 | Vagrant | Bobby Swim | James Williams | Virgil | 2:38 1/4 |
| 1875 | Aristides | Oliver Lewis | Ansel Anderson | Leamington | 2:37 3/4 |
**The Kentucky Derby was run at 1 1/2 miles until after the 1895 running, when it was changed to the current distance of 1 1/4 miles.
***Race record
(TC) denotes a Triple Crown winner
(f) denotes a filly
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