(AsiaGameHub) – Take a trip back in time by revisiting the four most significant upsets in Kentucky Derby history as we look ahead to tomorrow’s “Run for the Roses” at Churchill Downs in Louisville.
A quick note: Our picks are focused on racing’s modern era, so you can view each race right here on YouTube. For reference, Donerail remains the largest upset winner—this 91-1 longshot took first place in 1913.
Most Notable Kentucky Derby Upsets
We start our list with the most recent major upset in the Kentucky Derby.
2022 Rich Strike (80-1)
This upset sent ripples of surprise throughout the horse racing world.
Rich Strike was an also-eligible horse and wasn’t originally scheduled to compete. He got his spot only after Ethereal Road was pulled from the race the day prior, and owner Richard Dawson just made the entry deadline in time.
Jockey Sonny Leon guided Rich Strike to a win over top contenders Epicenter and Zandon in the final stretch. A $2 win wager on Rich Strike resulted in a $163.60 payout.
2019 Country House (65-1)
Country House was declared the winner of the 2019 Kentucky Derby after Maximum Security was disqualified due to interference. Stewards took over 20 minutes to make their ruling.
This disqualification (DQ) marked the first Derby win for jockey Flavien Prat and Hall of Fame trainer Bill Mott. Maximum Security was demoted from first to 17th place, finishing behind Long Range Toddy.
The teams behind Long Range Teddy and Country House both submitted interference claims.
Country House’s upset victory paid out $132.40 for a win bet.
2009 Mine That Bird (50-1)
Jockey Calvin Borel rode Mine That Bird from the back of the pack to first place in an impressive showing for owner Bennie Woolley Jr., who was competing in the Kentucky Derby for the first time.
Mine That Bird was the sole gelding in the 19-horse field. The unexpected Derby champion later finished second in the Preakness Stakes and third in the Belmont Stakes— the other two races that make up the Triple Crown.
A $2 win bet on Mine That Bird yielded $103.20. Back then, this was the highest payout since Donerail’s win in 1913.
2005 Giacomo (50-1)
Giacomo was owned and raised by legendary record producer Jerry Moss. Named for singer Sting’s son, Giacomo pulled off a huge upset against the 20-horse field.
Jockey “Money Mike” Smith rode Giacomo to victory, earning trainer John Shirreffs his first and only Kentucky Derby win. This was also Smith’s first Derby triumph, though he later won again with Triple Crown winner Justify in 2018.
Since Closing Argument finished second with 71-1 odds, this “Run for the Roses” set an exacta payout record of $9,814.80 that still holds true today.
Giacomo’s win resulted in a $102.60 payout for a win bet.
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