5 Biggest Kentucky Derby Upsets

In the exciting world of horse racing, there’s one thing you can always count on: unpredictability. 

One race that tends to guarantee a wild ride is the Kentucky Derby. In fact, this racing meet has such a long history of crazy outcomes that “Kentucky Derby upsets” has become an incredibly popular Google search on its own. 

So what is the Kentucky Derby? And why do Kentucky Derby upsets occur year on year? 

Let’s find out!

What is the Kentucky Derby?

Held annually on the first Saturday in May, the Kentucky Derby is an American Grade I stakes race run at Churchill Downs in Louisville. 

The race is 2km long, run by three-year-old thoroughbreds. The Kentucky Derby also goes by the name “The Run for the Roses,” as the winning horse is draped in a blanket of roses. 

Lasting approximately two minutes, the race is sometimes referred to as “The Most Exciting Two Minutes in Sports” or “The Fastest Two Minutes in Sports.” And due its fast pace and the young age of the horses, it holds a reputation as the craziest racing meet in the USA. 

With that in mind, we’re going to take a look at the biggest upset in Kentucky Derby history, along with some other great mishaps that have taken place at this race over its 48-year history. 

What Was the Biggest Upset Ever in the Kentucky Derby?

There are plenty of Kentucky Derby upsets to choose from! But we’re going to start with our favorite and then work our way down. 

So let’s start with the top spot….

Donerail, 1913

In what could be the greatest upset in Kentucky Derby history, Donerail stunned onlookers, and the entire US nation, at the 1913 race. Beating odds of 91-1, Donerail didn’t just win the race, he won it by half a length.

The reason why this particular Kentucky Derby upset was so impressive was because Donerail’s shocking triumph rewarded lucky bettors with a staggering $184.90 payout for a mere $2 wager. Even by today’s standards, that’s quite the payout. It’s also why it’s so important to understand odds when betting on horses. 

In addition, Donerail still holds the title of the longest shot in the history of the Kentucky Derby, cementing his place in the race’s history.

Animal Kingdom, 2011

The day before the 2011 Kentucky Derby, the anticipated favorite, Uncle Mo, withdrew from the race, leaving Dialed In as the lukewarm favorite at 5-1. But it wasn’t Dialed In that wowed the crowds that day, and a great Kentucky Derby horse upset was on its way. 

Animal Kingdom, disregarded at 21-1 odds, was the 11th choice in the lineup. Considered a long shot for good reason, until then he had only competed on turf and synthetic surfaces, with little experience on conventional dirt. However, as the race progressed, it became evident that Animal Kingdom was adapting well to the new terrain.

Apart from the substantial payout at double-digit odds, the real surprise stemmed from Uncle Mo’s withdrawal, which allowed a new champion to seize the spotlight. 

Animal Kingdom’s triumph marked the beginning of a successful career, culminating in a victory at the Dubai World Cup when he turned four.

Go for Gin, 1994

Torrential rain drenched the track before the 1994 Kentucky Derby, turning it into a muddy mess. 

Holy Bull, the favorite, had won eight out of nine starts and appeared poised for victory. However, the unexpected unfolded as Go For Gin reveled in the off-track conditions, stealing the race from the front and triumphing by two lengths at 9-1 odds.

While Holy Bull delivered a rare underwhelming performance, it was Go For Gin’s affinity for the sloppy track that led him to victory and left many scratching their heads. An outstanding upset pick for Kentucky Derby, if you were lucky enough to be there. 

Gato Del Sol, 1982

Gato Del Sol, the third-longest shot on the board at 21-1 odds, flew under everyone’s radar and pulled off a massive upset in the 1982 Kentucky Derby. Coming from last place, he rallied with extraordinary determination to win by 2 ½ lengths.

While Gato Del Sol had previously won the prestigious Del Mar Futurity as a juvenile, his three-year-old season had been less impressive. With no wins from four races and a fourth-place finish in the Santa Anita Derby, doubts loomed over whether his peak performance had passed him by.

Gato Del Sol defied generous odds to triumph, justifying the faith placed in him by trainer Eddie Gregson. As Gregson remarked to The New York Times in 1982, “I never stopped believing in this horse. Sometimes I doubted myself and the jockey, but never the horse.”

Lil E Tee, 1992

Jockey Pat Day was always known for his patience in the saddle, and the 1992 Kentucky Derby was no exception. Overlooked at odds of 17-1, Lil E Tee launched a bold bid from off the pace and won by a length. Behind him through eighth place, the other horses all finished with double-digit odds as well. 

Arazi, who wound up finishing eighth, was heralded as a super-horse in the making, and the betting public viewed him as nearly unbeatable as the odds-on favorite. The horse that seemingly had the potential to be his biggest challenger, A.P. Indy, had to defect from the race earlier in the week. Without that competition, Arazi seemed like a sure thing. 

However, Lil E Tee’s victory stunned the racing world as it watched wonder-horse, Arazi, finish eighth. In the history of Run for the Roses favorites, Arazi was one of the biggest, and he was beaten by what could be described as one of the best upset horse picks of Kentucky Derby.