Top 6 Best Kentucky Derby Upsets of All Time

Horse racing is known for its dramatic unpredictability, and as the most famous horse race in the world, the Kentucky Derby has had no shortage of incredible upsets. Over the course of decades, many horses have overcome huge odds to win the Run for the Roses, and here, we will take a look at the greatest upsets in Kentucky Derby history.

What are the Best Kentucky Derby Upsets of All Time?

1. Donerail (1913, 91-1 Odds)
2. Rich Strike (2022, 80-1 Odds)
3. Country House (2019, 65-1 Odds)
4. Mine That Bird (2009, 50-1 Odds)
5. Giacomo (2005, 50-1 Odds)
6. Canonero II (1971)
7. Honorable Mention: Mandaloun (2021, 27-1 Odds)

1. Donerail (1913, 91-1 Odds)

• 91-1 victory odds
• Longest official shot to win the Kentucky Derby

Donerail was the winner of the 39th running of the Kentucky Derby. Widely considered a huge longshot, he had won a few races as a two-year-old horse, including placing second in one competition to a favorite to win the 1913 Kentucky Derby, Foundation. Donerail’s owner, Thomas P. Hayes, was initially hesitant to enter his horse in the Derby. Since there was no space for him to be stabled at Churchill Downs, Donerail had to be housed three miles away, forcing him to walk three miles to the race over cobblestones. However, despite these disadvantages, Donerail managed the most impressive upset in Kentucky Derby history, overcoming the longest official odds ever recorded at the race to defeat the other seven running horses.

2. Rich Strike (2022, 80-1 Odds)

• 80-1 victory odds
• Second-longest odds to win in Kentucky Derby history
• Entered the race one day prior after Ethereal Road scratched

Rich Strike was the winner of the 148th Kentucky Derby, held on May 7, 2022. By tradition, Rich Strike, the horse with the longest odds in the race, was entered into the starting gate last, being the twentieth horse to enter the race. Astonishingly, Rich Strike had not even been scheduled to run in the Derby and was only entered the day before the race due to one of the scheduled horses, Ethereal Road, dropping out of contention. As the race went off, Rich Strike was in the middle of the pack, at one point placing 18th and still in 15th place with only a quarter of a mile to go. However, Rich Strike’s jockey, Sonny Leon, managed to maneuver the horse to the inside rail as the race entered its final stretch. With a huge burst of speed, Rich Strike darted around the leading horses to pass the race’s two favorites and frontrunners–Epicenter and Zandon–at the last moment, securing an unbelievable win.

3. Country House (2019, 65-1)

• 65-1 victory odds
• First horse to win the Kentucky Derby after crossing the finish line second
• Won as a result of Maximum Security’s disqualification for a racing foul

Country House was the winner of the 145th Kentucky Derby. The incredible underdog victory is notable in two ways: firstly for its long odds, and secondly, for its historical importance. At 65-1 odds, Country House was hardly expected to place in the Derby, but in addition to these long odds, he was not even the horse who crossed the finish line first. In fact, the 2019 Kentucky Derby was historic because it became the first-ever Derby where the horse that crossed the finish line first did not win. That horse, Maximum Security, was initially thought to have won, but race officials soon disqualified him for veering off at the beginning of the stretch. Maximum Security’s actions were deemed a foul, as they interfered with other horses in the race, and his victory was expunged. This stunning ruling, the first of its kind in Derby history, makes Country House’s win one of the most shocking upsets in the long line of Kentucky Derby races. 

4. Mine That Bird (2009, 50-1)

• 50-1 victory odds
• Fifth-widest margin of victory for any Kentucky Derby winner (6 ¾ lengths)
• Largest margin of victory in the previous 60 years

Mine That Bird was the winner of the 135th Kentucky Derby. A promising horse with four straight wins as a two-year-old and two solid performances at three, Mine That Bird was nonetheless given very long odds to win the 2009 Kentucky Derby. Much like Rich Strike in 2022, Mine That Bird began his running of the Derby in last place and was only mentioned by name once during the live call. However, despite being far behind the pack, Mine That Bird took off in the final stretch, running the inside rail of the track so fast that the announcers barely noticed him until he had already passed the frontrunners. After that, Mine That Bird completed a stunning six and ¾-length victory, the fifth-widest margin in Kentucky Derby history.

5. Giacomo (2005, 50-1)

• 50-1 victory odds
• Won by only half of a length
• First Derby win for famed jockey Mike Smith

Giacomo was the winner of the 131st Kentucky Derby. Owned by Jerry Moss, a famous music executive, Giacomo was not considered an extremely impressive horse. Most gamblers did not think he had what it took to match the better-looking horses at the Kentucky Derby in 2005. When he first entered the race, Giacomo had only one previous victory, and as with many of our other upsets, he began the race near last place and remained there through the backstretch. However, guided by jockey Mike Smith–whose many racing victories would include a Triple Crown win on Justify thirteen years later–Giacomo managed to close in on the frontrunners along the outside of the track and managed a mere half-length victory to score a stunning upset, which was also Mike Smith’s first-ever Kentucky Derby win.

6. Canonero II (1971)

• No official odds of victory
• Purchased as a yearling for $1200, and considered so unimpressive that he was not given official odds to win the Kentucky Derby
• Later won the 1971 Preakness Stakes

Canonero II was the winner of the 97th Kentucky Derby. A horse who was considered rather unimpressive, he had been purchased as a yearling for only $1200 and was raised in Venezuela with a poor racing record. Nevertheless, Canonero II’s trainer, Juan Arias, decided to enter him in the Kentucky Derby, where many bettors dismissed him as being extremely out of his league. Canonero II was considered so unfit to run in the Derby that he was not even given official odds and was instead lumped into a “mutual field” of six horses that were considered long shots and could thus be bet on together rather than individually. Had he been a standalone entrant, Canonero II may have fetched odds of 100-1. However, none of the disdain for him stopped Canonero II from performing a massive upset, winning the Kentucky Derby of 1971 and the Preakness Stakes that same year, though he did not complete the Triple Crown. 

7. Honorable Mention: Mandaloun (2021, 27-1)

• 27-1 victory odds
• Won as a result of Medina Spirit’s disqualification for high levels of anti-inflammatory drugs
• First-time Derby win for trainer Brad Cox, jockey Florent Geroux, and owner Juddmonte

Mandaloun was the winner of the 147th Kentucky Derby. Mandaloun’s upset win deserves an honorable mention here due to the unusual circumstances that led to it. Though his second-place finish in the race itself was impressive enough for a horse with 27-1 odds, Mandaloun became famous soon after the 2021 Kentucky Derby ended as a result of the scandal which embroiled the race’s first-place finisher, Medina Spirit. Trained by the famed Bob Baffert, Medina Spirit performed well in the Derby, crossing the finish line first. However, one day after his win, Medina Spirit tested positive for high levels of an anti-inflammatory drug that may have improved his performance. The test results led to a suspension for Bob Baffert, and after much deliberation, Medina Spirit was stripped of his victory, which was officially awarded to Mandaloun.