The Kentucky Derby wouldn’t be the Kentucky Derby without Americans betting an exorbitant amount of money on the race. Each year, many viewers take their chances on a longshot in hopes of a huge payout.

Most years, it doesn’t pay off. The favorites are the favorites for a reason, and the winner isn’t typically completely out of left field even if the frontrunner doesn’t win.

That isn’t the case every year, though. In fact, two of the biggest upsets in Kentucky Derby have occurred in the last five years. That list got a new member in 2022, when Rich Strike shocked the rest of the field and won as a massive underdog. Is another longshot poised to join the ranks this year?

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The Sporting News takes a look at the biggest upsets in the long history of the Kentucky Derby. 

Biggest upsets in Kentucky Derby history

Rich Strike wasn’t the largest underdog to ever win the Kentucky Derby, but it was the biggest upset in 109 years. Donerail’s 1913 win as a 91-1 longshot still stands alone as the biggest upset in the history of horse racing’s biggest event. 

Aside from Donerail, most major Kentucky Derby upsets have been recent. Six of the 10 biggest upsets have occurred in the 21st century, and two of the top three have happened in the last five years. Country House’s 2019 victory came with an extra shot of controversy, as Maximum Security crossed the finish line first but was disqualified for interference. 

After Donerail, Rich Strike, and Country House, Giacomo (2005), and Mine That Bird (2009) are the only other winners in Kentucky Derby history to enter with 50-1 odds or worse. 

Rich Strike spent a long portion of the race buried in the pack before jolting ahead out of nowhere to claim an unlikely win. As upsets continue to pile up this century, it might not be long until we see another horse join the list. 

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Below is a look at the 10 biggest upsets in Kentucky Derby history.