Five of the Biggest Upsets in Kentucky Derby History

The 152nd Kentucky Derby is taking place Saturday, May 2, at Churchill Downs. The 20-horse field is set with Arkansas Derby Winner Renegade (4-1) as the early favorite.

Recent history has shown that picking the favorite has not worked out so well for Kentucky Derby bettors. If you're curious about the last time the favorite won the Run for the Roses, the correct answer would be 2018. Justify, trained by Bob Baffert, won the race and went on to win horse racing’s Triple Crown.

When it comes to Kentucky Derby history, dating all the way back to 1908, the post-time favorite has only won 40 times.

Instead of highlighting those 40 favorites, we’re looking back at some of the greatest horse racing underdog stories of all time. One even takes us back all the way to 1913, as Donerail’s win remains the biggest upset in the event’s 150-plus years. With the 2026 Kentucky Derby fast approaching, we look back at five horses that went from unknowns to winners on the sport’s grandest stage.

Will a favorite win the 2026 Kentucky Derby?

The field for the 152nd Kentucky Derby is set as the post position draw was held on Saturday afternoon. Here is a look at this year’s field along with the morning line odds. As of Saturday, Renegade Florida Derby winner Commandment and Further Ado, the top finisher at the Blue Grass Stakes, were the early favorites.

*Mandaloun was declared the 2021 Kentucky Derby winner after Medina Spirit was stripped of the title due to a failed drug test. 

Five Biggest Upsets in Kentucky Derby History 

Some of the greatest stories in Kentucky Derby history are those involving a huge underdog shocking the field. You know, the horse that barely gets mentioned when talking about the favorites. However, the first leg of the Triple Crown is often referred to as “the greatest two minutes in sports,” and the five horses highlighted below are great examples of why.

Donerail, 91-1 (1913)

Imagine if the 1913 race were held today, and what the call would sound like. More than a century later, Donerail’s victory remains the biggest upset in Kentucky Derby history. Eight horses made the field, but nobody expected Donerail, the 91-1 extreme longshot, to win. He won the race by a half-length. A $2 bet on Donerail to win paid $184.90. The Kentucky Derby victory ended up being one of only 10 career wins.

Rich Strike, 80-1 (2022)

The second biggest upset in Kentucky Derby history took place in 2022. Rich Strike, an 80-1 underdog, had the longest odds out of the 20 horses and wasn't expected to even be in the conversation with the likes of Epicenter (7-2) and Zandon (3-1), who finished second and third, respectively. Ironically, Rich Strike was not slated to start as he was an alternate and was added after Ethereal Road scratched. If you listen to the replay, the announcer doesn't even mention Rich Strike until the final stretch – a $2 bet on Rich Strike to win paid $163.60.

Country House, 65-1 (2019)

The other major Kentucky Derby shocker from the last decade was Country House’s 2019 win. However, this one included a controversial finish in which winner Maximum Security was disqualified for an in-race foul. Bettors wagered over $6.2 million on Maximum Security, who had 9-2 odds, to win bets. This was the first time in the race’s 145-year history that a winner was disqualified because of interference. Country House was declared the winner, and those $2 to win bets paid $132.40. 

Mine That Bird, 50-1 (2009)

Mine That Bird’s 2009 win was a historic moment for trainer Bennie Woolley Jr., as this was his first time running a horse in the Kentucky Derby. On the rain-soaked course, Mine That Bird was the one that rallied from the back of the field all the way to first. In 2008, he finished last in the Breeders’ Cup Juvenile that had a 12-horse field. Talk about a storybook moment to shine in front of the horse racing world, Mine That Bird pulled away from the field and won by 6 ¾ lengths. At the time, the $103.20 return on winning tickets was the second-highest ever behind the Donerail payout. 

Giacomo, 50-1 (2005) 

The 2005 Kentucky Derby stands out because longshots dominated the race, with Giacomo (50-1) finishing first and Closing Argument (70-1). Bellamy Road, the 5-2 favorite, had won four of his first five races prior to this one, including the Wood Memorial. Bellamy Road ended up finishing seventh. After three-quarters of a mile, Giacomo was sitting 18th in the 20-horse field. He ended up beating Closing Argument by a half length for a payout of $102.60.

Final countdown to 152nd Kentucky Derby

The Kentucky Derby is one of those great annual sporting events that brings a crowd of 150,000-plus spectators to Churchill Downs every year. Fans come dressed to impress, wearing stylish, crazy hats. There is even a “What to Wear” section on the Kentucky Derby website.

Then there is the national television audience of millions glued to the screen watching a race that takes about two minutes from start to finish, with thousands—potentially millions—of fans wagering on horse racing betting sites.

Post time is approximately 6:57 p.m. EST. No matter if a favorite or underdog wins, there will be another exciting chapter added to the Kentucky Derby history books.