How Often Do Kentucky Derby Winners Also Win Preakness Stakes?

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Written By Eli Hershkovich | Last Updated
Preakness Odds

Established at Pimlico Race Course in 1873, the Preakness Stakes was named after the first horse that won the Dinner Party Stakes in 1870. The second jewel of horse racing’s Triple Crown returns on Saturday, May 18, with Mystik Dan one-third of the way toward history if trainer Kenny McPeek gives him the opportunity. With that in mind, how often have Kentucky Derby winners also cashed in for bettors backing their Preakness Stakes odds? Let’s delve into Preakness history.

Preakness history: First Two Legs Of Triple Crown

Beyond the thirteen Triple Crown winners, there have been 23 horses to emerge victorious in the Kentucky Derby and Preakness Stakes — before falling short at the Belmont Stakes. Most recently, I’ll Have Another won the 2012 Derby and the Preakness with thrilling stretch drives. Nevertheless, he was scratched from the Belmont with an injury. He was the 4-5 early favorite to win the Belmont and become the first Triple Crown winner since Affirmed in 1978.

Of course, Justify (2018) and American Pharoh (2015) have won the most recent Triple Crowns after I’ll Have Another bowed out of his opportunity.

Here are the 13 horses to claim the illustrious American Triple Crown:

  • Justify (2018)
  • American Pharoah (2015)
  • Affirmed (1978)
  • Seattle Slew (1977)
  • Secretariat (1973)
  • Citation (1948)
  • Assault (1946)
  • Count Fleet (1943)
  • Whirlaway (1941)
  • War Admiral (1937)
  • Omaha (1935)
  • Gallant Fox (1930)
  • Sir Barton (1919)

Below are the 23 who only delivered at the first two prestigious events:

  • Bold Venture (1936)
  • Pensive (1944)
  • Tim Tam (1958)
  • Carry Back (1961)
  • Northern Dancer (1964)
  • Kauai King (1966)
  • Forward Pass (1968)
  • Majestic Prince (1969)
  • Canonero II (1971)
  • Spectacular Bid (1979)
  • Pleasant Colony (1981)
  • Alysheba (1987)
  • Sunday Silence (1989)
  • Silver Charm (1997)
  • Real Quiet (1998)
  • Charismatic (1999)
  • War Emblem (2002)
  • Funny Cide (2003)
  • Smarty Jones (2004)
  • Big Brown (2008)
  • I’ll Have Another (2012)

So in the 21st century, only seven horses have won the Derby and Preakness and none since 2018. That’s five consecutive years where the Derby winner has failed to find the winner’s circle two weeks later.

Frequency Of Cashing In

Between the 36 horses who turned the Derby-Preakness double, including the 13 Triple Crown winners and the 26 Derby winners who hit the board at Pimlico, there have been 62 who wore the garland of roses at Churchill Downs who landed on win, place, or show tickets for the Triple Crown’s middle jewel. A slew of Derby winners have also underperformed at Pimlico. In fact, 22 failed to hit the board, including Always Dreaming (eighth-place finish) in 2017.

Last year, Mage came in third, finishing just inside this elusive standing. His effort helped produce a 74.1% hit rate of Derby winners who have also placed in the money at the Preakness Stakes.

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*Some information courtesy of Pimlico Racing News and press releases