These Are the Biggest Upset Wins in Kentucky Derby History

The fastest two minutes in sports delivered a thrilling finish last year with Rich Strike completing the second-biggest upset in Kentucky Derby history. 

The thoroughbred entered the race as an alternate and joined an elite club of horses that have shocked Churchill Downs. 

Here are some of the racing horses that overcame the odds to win the sport’s biggest race, the Kentucky Derby. 

Donerail (1913)

Odds: 91-1

The 39th winner of the Kentucky Derby earned his roses. While Donerail had shown promise in the year leading up to the Derby, owner Thomas P. Hayes required some convincing to make the trip to Louisville. Once at Churchill Downs, they stabled Donerail at Douglas Park due to overcrowding and required him to walk the three miles on dirt and cobblestone on the day of the race. 

Hayes, focused primarily on the financial payouts, reportedly told jockey Roscoe Goose to get a piece of the purse by crossing in one of the top-5 spots. Goose and Donerail certainly got a piece, passing the favorites, Ten Point and Yankee Notion. 

Rich Strike (2022)

Odds: 80-1

Forty-eight hours before the race, Rich Strike was nowhere near the conversation of Kentucky Derby champions. In fact, he wasn’t even in the same race. As fate would have it, Ethereal Road scratched and that opened the door for Rich Strike and trainer Eric Reed. 

Unlike some years, the favorites -- Epicenter and Zandon -- finished second and third, respectively, but didn’t have an answer for Rich Strike down the stretch. This upset delivered a $163.60 payout.

Country House (2019)

Odds: 65-1

Country House’s run was historic in more ways than one. Not only did he overcome insurmountable 65-1 odds, but his victory marked the first time in the 145-year history of the Derby that the horse to cross the finish line first -- Maximum Security -- did not in fact win. 

In the immediate aftermath of the race, an objection was raised against Maximum Security, accusing him and jockey Luis Saez of interfering with several horses down the final straightaway. While Country House was not one of the impacted horses, he crossed the finish line second and earned the win with the disqualification of Maximum Security.

Mine That Bird (2009)

Odds: 50-1

The first time Mine That Bird was mentioned in the race was near the midway point, when NBC announcer Tom Durkin noted he was “well behind the rest of them,” sitting in a distant last place. What transpired was one of the greatest comebacks in Derby history.

Down the final straight, Mine That Bird came seemingly out of nowhere to position himself along the inside of the track and charge past the field to claim the largest margin of victory in over 60 years.

Giacomo (2005)

Odds: 50-1

Owned and bred by music executive Jerry Moss, Giacomo had done little to suggest that he was ready to compete among the heavyweights. He entered the Kentucky Derby with only one win to his name, secured at a maiden race, he hung with a field that went out at blistering pace. He gained speed down the stretch and pulled out in front of a three-horse photo finish.

Charismatic (1999)

Odds: 31-1

One of the more bittersweet stories in horse racing, Charismatic nearly completed the Triple Crown, but fell short with an injury at the Belmont Stakes and never raced again.

His journey, however, began in Louisville, overcoming 31-1 odds. He and jockey Chris Antley strategically navigated the field and came out victorious. 

After winning the Preakness Stakes, Charismatic gained favorite status heading into the Belmont Stakes. He led down the stretch and seemed poised to capture the third and final piece of the Triple Crown before pulling up with an apparent injury and finishing third. The image of Antley cradling his leg to prevent further injury was famously etched in the lore of horse racing as what could have been. 

Thunder Gulch (1995)

Odds: 25-1

Another thoroughbred that came just shy of Triple Crown glory, Thunder Gulch won the Kentucky Derby and Belmont Stakes in 1995. While his victory at Churchill Downs was considered a fluke by some, he backed it up with a win in New York and narrow loss in Baltimore. 

Animal Kingdom (2011)

Odds: 21-1

The 2011 Kentucky Derby was a meeting of the most unlikely odds for thoroughbred Animal Kingdom and jockey John R. Velasquez. 

In the leadup to the Derby, Velasquez was informed that Uncle Mo, a leading contender, would not race as he recovered from a stomach infection. Meanwhile, trainer Graham Motion was forced to sit Toby’s Corner and turn all his attention to Animal Kingdom, the underdog of the two options.  

These obstacles brought the two sides together in a race that would jump start Velasquez’s legendary career. He said he felt comfortable right out the gate and rode that confidence to the finish line. 

Velasquez won the Derby three more times in 2017, 2020 and 2021. However, his 2021 victory with Medina Spirit was later vacated after the horse tested positive for Betamethasone, an anti-inflammatory ointment banned beyond therapeutic purposes. 

War Emblem (2002)

Odds: 21-1

Before there was Animal Kingdom, there was War Emblem. 

Jockey Victor Espinoza’s first introduction with the horse came on the day of the race, but that didn’t keep the duo from winning the 128th Running of the Roses. They jumped out to an early lead and held off challengers. 

Espinoza won the Kentucky Derby two more times, in 2014 with California Chrome and 2015 with American Pharoah.

Lil E. Tee (1992)

Odds: 17-1

The prize-winning horse, nicknamed E.T., came from humble beginnings, overcoming numerous health issues including an immune deficiency, a bad case of colic and an emergency surgery that nearly killed him.

He ended up in the care of Cal Partee and picked up several impressive wins en route to the Kentucky Derby. At Churchill Downs, he overcame a stacked field that included Arazi, frequently compared to Secretariat.