Biggest Kentucky Derby Upsets in History

Biggest Kentucky Derby Upsets in History
Image © Michael Clevenger and O'Neil Arnold/Courier Journal / USA TODAY NETWORK
✍️ Written by
Frank Weber
🗓 Updated
Aug 2nd 2023

Unless you live under a rock, you know the Kentucky Derby was run this weekend–and what a race it was. My pick was Mo Donegal, who got off to an awful start and found herself at the back of the pack very early on. She was able to make a bit of a push and finished top 5, but none of it mattered–all because of Rich Strike.

The 80-1 underdog just found out they were racing in the Derby a mere 48 hours before the race even kicked off. However, after Ethereal Road scratched, Rich Strike was given their opportunity–and they did not let it slip.

Strike finished first in front of Epicenter and Zandon–the race's two favorites. Rich Strike was the biggest underdog in the field sitting at 80-1, but it begs the question–is it the biggest upset in Kentucky Derby history? Why don’t we take a look.

Well BEFORE we take a look, I think it’d be foolish of me to not talk about where you can bet on these horseraces. It’s all dependent on what state you are in, but TwinSpires is one of the most widespread horse bettings apps/operators on the market. However, some of the most popular sports betting operators (such as DraftKings) are able to offer horse racing odds in select states.

One of the best sportsbooks on the market is BetMGM Sportsbook. If you use promo code ODDSSEEKER upon registration, you receive an (up to) $1000 risk-free bet.

Biggest Upsets in Derby History

Donerail (1913)

Odds: 91-1

It’s crazy to think that the Derby back in 1913 was the 39th ever Derby–but that just goes to show you how long this race has been going on. As the story goes, Donerail was a very competitive horse and would have had higher odds in normal conditions–however, due to overcrowding Donerail had to be stabled at Douglas Park, which was 3 miles away from Churchill Downs.

Donerail had to walk three miles on dirt and cobblestone the day of the race, but was able to come away with the victory.

Rich Strike (2022)

Odds: 80-1

We know the story. 48 hours before the race, Rich Strike was nowhere near the conversation for winning the Derby–she wasn’t even IN the derby. However, fast forward two days and look at who was biting at the leg of a race marshall on the way to the winner's circle.

Country House (2019)

Odds: 65-1

Country House is a double history maker–not only did they overcome great odds, but they were the first-ever horse to win the race, despite not crossing the finish line first. Maximum Security, the initial winner of the race, was later disqualified due to interference down the final stretch.

Country House landing second was a feat in and of itself, but the cherry on top came after Maximum Security’s disqualification.

Mine That Bird (2009)

Odds: 50-1

Not only was Mine That Bird an afterthought before the fight–they were an afterthought DURING the fight. Within the first half-mile, Mine That Bird was nowhere near the rest of the pack. However, down the final straight, Mine That Bird came seemingly out of nowhere to position itself along the inside of the track and take first place.

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