Take a walk down memory lane by reliving the four biggest upsets in Kentucky Derby history ahead of tomorrow’s “Run for the Roses” at Churchill Downs in Louisville.
One caveat: Our selections are based on racing’s modern era, so you can watch each race here on YouTube. For the record, Donerail is the biggest upset winner after the 91-1 longshot finished first in 1913.
Biggest Kentucky Derby Upsets
Our list begins with the most recent monumental upset in the Kentucky Derby.
2022 Rich Strike (80-1)
This one sent shockwaves through the horse racing industry.
As an also-eligible horse, Rich Strike wasn’t even slated to start the race. He gained entry only when Ethereal Road was scratched the day before. Owner Richard Dawson barely met the deadline to enter him.
Jockey Sonny Leon piloted Rich Strike to victory over favorites Epicenter and Zandon down the stretch. A $2 win bet on Rich Strike returned a $163.60 payout.
2019 Country House (65-1)
Country House was determined to be the winner of the 2019 Kentucky Derby after Maximum Security was disqualified for interference. It took the stewards more than 20 minutes to render their decision.
The DQ gave jockey Flavien Prat and Hall of Fame trainer Bill Mott their first Derby wins. Maximum Security was relegated from first to 17th place behind Long Range Toddy.
The connections of Long Range Teddy and Country House both filed interference claims.
Country House delivered a $132.40 payout for the upset win.
2009 Mine That Bird (50-1)
Jockey Calvin Borel carried Mine That Bird from last to first in a stunning performance for owner Bennie Woolley Jr., who was making his debut in the Kentucky Derby.
Mine That Bird was the only gelding in the 19-horse field. The surprise Derby winner went on to finish runnerup in the Preakness Stakes and third in the Belmont Stakes, the other two races that round out the Triple Crown.
Mine That Bird paid $103.20 on a $2 win bet. At the time, that was the most since Donerail in 1913.
2005 Giacomo (50-1)
Giacomo was owned and bred by the legendary record producer Jerry Moss. Named after the son of singer Sting, Giacomo stung the 20-horse field with a massive upset.
“Money Mike” Smith rode Giacomo to the victory to give trainer John Shirreffs his first and only Kentucky Derby victory. It was also Smith’s first Derby win, but he went on to win again with Triple Crown winner Justify in 2018.
With Closing Argument finishing second at 71-1, this “Run for the Roses” produced an exacta payout record of $9,814.80, which stands today.
Giacomo returned $102.60 for the victory.
