KENTUCKY DERBY WINNERS VS. KENTUCKY DERBY WINNERS Winners of the Kentucky Derby have faced each other 43 times. The races have occurred 17 times in New York, nine in California, nine in Maryland, six in Kentucky, one in Illinois and one in Canada. Derby winners have run 1-2 on 12 occasions. The older Derby winner has prevailed 24 times. Three Kentucky Derby winners have been pitted against one another twice, including a 1-2-3 finish in the 1918 Bowie Handicap at Pimlico by George Smith, Omar Khayyam and Exterminator. Exterminator raced against Derby winners 15 times and finished ahead of his rose-bearing rivals nine times. His chief competitor was Paul Jones, who he beat in seven of 10 races while carrying more weight in each affair. Date Track Race Distance Derby Winner (Age, Weight) Finish Derby Winner (Age, Weight) Finish Nov. 2, 1991 Churchill Downs Breeders’ Cup Classic 1 ¼ M Unbridled (4, 126) 3rd Strike the Gold (3, 122) 5th June 26, 1988 Hollywood Park Hollywood Gold Cup H. 1 ¼ M Alysheba (4,126) 2nd Ferdinand (5, 125) 3rd April 17, 1988 Santa Anita San Bernardino H. 1 1/8 M Alysheba (4, 127) 1st Ferdinand (5, 127) 2nd March 6, 1988 Santa Anita Santa Anita H. 1 ¼ M Alysheba (4, 126) 1st Ferdinand (5, 127) 2nd Nov. 21, 1987 Hollywood Park Breeders’ Cup Classic 1 ¼ M Ferdinand (4, 126) 1st Alysheba (3, 122) 2nd Oct. 6, 1979 Belmont Park Jockey Club Gold Cup 1 ½ M Affirmed (4, 126) 1st Spectacular Bid (3, 121) 2nd Oct. 14, 1978 Belmont Park Jockey Club Gold Cup 1 ½ M Seattle Slew (4, 126) 2nd Affirmed (3, 121) 5th Sept. 16, 1978 Belmont Park Marlboro Cup 1 1/8 M Seattle Slew (4, 128) 2nd Affirmed (3, 124) 2nd Sept. 15, 1973 Belmont Park Marlboro Cup 1 1/8 M Secretariat (3, 124) 2nd Riva Ridge (4, 127) 2nd Sept. 20, 1972 Belmont Park Stymie H. 1 1/8 M Canonero II (4, 110) 1st Riva Ridge (3, 123) 2nd Aug. 6, 1964 Saratoga Schenectady Purse 7 F Chateaugay (4, 124) 1st Decidedly (5, 124) 2nd June 11, 1955 Hollywood Park Californian 1 1/16 M Swaps (3, 115) 1st Determine (4, 126) 2nd Dec. 9, 1950 Hollywood Park Hollywood Gold Cup 1 ¼ M Ponder (4, 125) 5th Assault (7, 121) 7th Feb. 25, 1950 Santa Anita Santa Anita H. 1 ¼ M Citation (5, 132) 2nd Ponder (4, 124) 4th Feb. 11, 1950 Santa Anita San Antonio H. 1 1/8 M Ponder (4, 128) 1st Citation (5, 130) 2nd May 16, 1930 Churchill Downs Shady Brook Farm H. 1 1/16 M Whiskery (6, 108) 2nd Clyde Van Dusen (4, 112) 10 th April 28, 1923 Havre de Grace Old Dominion H. 1 M 70 Y Exterminator (8, 132) 2nd Paul Jones (6, 108) 3rd April 21, 1923 Havre de Grace Philadelphia H. 1 1/16 M Exterminator (8, 129) 1st Paul Jones (6, 108) 2nd Nov. 11, 1922 Pimlico Pimlico Cup H. 2 ¼ M Paul Jones (5, 99) 2nd Exterminator (7, 126) 3rd Oct. 28, 1922 Laurel Park Washington H. 1 ¼ M Exterminator (7, 132) 4th Paul Jones (5, 106) 7th Aug. 27, 1921 Saratoga Merchants and Citizens’ H. 1 3/16 M Exterminator (6, 130) 1st Paul Jones (4, 109) 5th June 17, 1921 Aqueduct Brooklyn H. 1 1/8 M Exterminator (6, 129) 3rd Paul Jones (4, 116) 10 th June 4, 1921 Belmont Park Suburban H. 1 ¼ M Exterminator (6, 133) 5th Paul Jones (4, 118) 8th Nov. 12, 1920 Pimlico Pimlico Cup H. 2 ¼ Exterminator (5, 126) 1st Paul Jones (3, 110 ½) 3rd Nov. 8, 1920 Pimlico Bowie H. 1 ½ M Paul Jones (3, 120) 4th Exterminator (5, 135) 5th Aug. 2, 1920 Saratoga Saratoga H. 1 ¼ M Sir Barton (4, 129) 1st Exterminator (5, 126) 2nd June 5, 1920 Belmont Park Suburban H. 1 ¼ M Paul Jones (3, 106) 1st Exterminator (5, 123) 3rd Sept. 27, 1919 Havre de Grace Havre de Grace H. 1 1/8 M Exterminator (4, 126) 2nd Sir Barton (3, 124) 3rd Nov. 12, 1918 Pimlico Bowie H. 1 ½ M George Smith (5, 130) 1st Omar Khayyam (4, 115) 2nd Exterminator (3, 120) 3rd Oct. 12, 1918 Laurel Park Washington H. 1 1/8 M Exterminator (3, 113 ½) 3rd Omar Khayyam (4, 127) 4th Aug. 1, 1917 Saratoga Saratoga H. 1 ¼ M George Smith (4, 117) 4th Old Rosebud (6, 132) 5th June 25, 1917 Aqueduct Brooklyn H. 1 1/8 M Regret (5, 122) 2nd Old Rosebud (6, 120) 3rd Omar Khayyam (3, 110) 10 th Sept. 16, 1912 Douglas Park Douglas Park Inaugural H. 1 1/16 M Wintergreen (6, 107) 8th Donau (5, 106) Left Aug. 12, 1912 Hamilton, Ontario Handicap for 3 & up 6 F Worth (3, 119) 3rd Wintergreen (6, 113) 5th June 25, 1910 Latonia Brewers’ Exchange H. 6 F Wintergreen (4, 117) 3rd Donau (3, 112) 8th June 5, 1905 Gravesend Handicap for 3 & up 1 1/16 M Alan-a-Dale (6, 122) 4th Elwood (4, 104) 8th Feb. 24, 1904 Los Angeles JC Selling race $400 purse 1 1/16 M His Eminence (6, 104) 4th Elwood (3, 101 or 102) 5th Sept. 29, 1897 Gravesend All-age race 1 1/16 M Plaudit (2, 90) 1st Ben Brush (4, 126) 2nd Aug. 18, 1888 Saratoga Handicap Sweepstakes 1 ½ M Montrose (4, 118) 1st Macbeth II (3, 102) 4th July 3, 1888 Washington Park Boulevard 1 ¼ M Montrose (4, 113 or 118) 2nd Macbeth II (3, 109) 6th June 2, 1888 Latonia Distillers’ & Brewers’ 1 M 500 Y Montrose (4, 115) 1st Macbeth II (3, 103) 3rd May 7, 1888 Kentucky Association Distillers’ 1 ¼ Macbeth II (3, 94) 2nd Montrose (4, 118) 4th Oct. 7, 1887 Jerome Park Free Handicap Sweepstakes 1 1/16 M Ben Ali (4, 118) 1st Joe Cotton (5, 112) 3rd .