Kentucky Derby: 5 of the Biggest Upsets in Kentucky Derby History
The first Saturday in May is a key date in the diary for all sports fans, as the eyes of the world will be on Churchill Downs for the opening leg of the Triple Crown.
The Kentucky Derby brings together the very best horses aged three on the dirt, with the winner of the Derby being immortalized forever in the history books. Greats such as American Pharoah, Secretariat, and Whirlaway have all won the Run for the Roses, but sometimes there are unlikely tales that play out on the track.
Therefore, it is always worth considering the long shots in the Kentucky Derby. But, what are the 5 biggest upsets in Kentucky Derby history?
5 Biggest Upsets in Kentucky Derby History
1. Donerail (+9100)
The most famous long shot to win the Kentucky Derby came back in 1913, when Donerail defied odds of +9100 to win the opening leg of the Triple Crown. Trained by Thomas P. Hayes, the McGee colt was given no chance to win the prestigious race.
Hayes also had reservations about running the horse, as Donerail was stabled at nearby Douglas Park due to not enough space at Churchill Downs. However, the trainer would be rewarded for running his stable star, with Donerail drawing away from the field to win in a then-track record time of 2:04 4/5.
2. Rich Strike (+8000)
It would be nearly 100 years later before Donerail’s biggest upset in Kentucky Derby history tag would be tested, as Rich Strike would shock the world at Churchill Downs in 2022 to win at odds of +8000. The victory would give Sonny Leon and Eric Reed their first Triple Crown race wins.
His victory was all the more shocking considering that his place in the gates wasn’t confirmed until 24 hours before the Derby when Ethereal Road was scratched. Therefore, he is the only Derby winner in history not to be included in merchandise for the race.
3. Country House (+6500)
One of the most contentious results in the Kentucky Derby also led to one of the greatest upsets, as Country House was deemed the winner in 2019 following the disqualification of Maximum Security. The Lookin at Lucky colt was sent off at odds of +6500, and was awarded the race after Maximum Security was deemed to have interfered with several horses.
The 2019 Derby made history by becoming the first edition to feature a runner-up being upgraded to the winner following in-race interference. Overall, it is only one of three occasions in Derby history where the first-place finisher has been changed due to a DQ, with the others being Forward Pass in 1968 and Mandaloun in 2021.
4. Mine That Bird (+5000)
Deep closers always give bettors a thrill, but few could have foreseen +5000 outsider Mine That Bird going from last to first in the stretch in the Kentucky Derby to win by six lengths in 2009.
The Chip Woolley-trained Derby winner created one of the most famous stories in Derby history, with the runner traveling from New Mexico, completing a 21-hour journey to compete in the race. His acclaimed success was the plot for the movie ’50 to 1’, starring Skeet Ulrich, Christian Kane, and William Devane.
5. Giacomo (+5000)
One of the biggest upsets in Kentucky Derby history came in 2002, as Giacomo became the fourth-biggest priced winner of the opening leg of the Triple Crown race.
The three-year-old by Holy Bull was a likable grey, trained by the legendary John Shirreffs. Giacomo rallied from the back of the chasing pack to finish just under a length clear of Closing Argument. A third in the Preakness Stakes a month later ended Triple Crown dreams, but he did scoop big prize money before his retirement in the 2006 G2 San Diego Handicap.
After considering the biggest upsets in Kentucky Derby history, you can learn more about the runners involved in the Kentucky Derby in 2026.
