Greatest Upsets in Horse Racing History

min read
two jockeys racing on their horses on a green grass horse racing track
BetMGM @BETMGM Jun 08, 2023, 11:00 AM

Imagine the thrill of the world’s biggest and most lucrative horse races, where anything can happen. It’s that electrifying moment when an unknown colt or filly goes from being an underdog to a true legend in just two short minutes. This very excitement keeps us glued to online sports betting.

Defining an Upset

To understand why horse racing upsets are so significant, we must first define an “upset.” The term “upset” refers to an unforeseen or unsuspected outcome, often seen in sports competitions. The sport of horse racing is no stranger to such surprises, which bring excitement to the sport and bring unexpected joy to savvy bettors.

Let’s revisit some of the most incredible and financially rewarding longshots in thoroughbred horse racing history.

1. Arcangues (1993)

Arcangues (pronounced “Ar-kong”) was bred in France, where he was already champion at many stakes, including the Prix d’Ispahan. His owner was a French art dealer called Daniel Wildenstein. However, despite his success in France, Arcangues was overlooked in the star-studded, 14-horse field of the Breeders’ Cup Classic, which included favorites like Bertrando. His odds were a staggering +13,300!

As the grueling mile-and-a-quarter race began, Arcangues started off trailing behind as Bertrando took the lead and held it for an impressive 7 furlongs. 

But then the unexpected began to unfold. Bertrando started to fade and Arcangues seized the opportunity, surging along the rail to take the lead. In an incredible display of strength, Arcangues crossed the finish line two lengths ahead of Bertrando. Can you imagine the excitement if you had placed a $2 win ticket on Arcangues?

2. Rockamundo (1993)

The 1993 Arkansas Derby was a bit out of Rockamundo’s league in the graded event. He had just one win in nine starts and disappointing losses leading up to the race. He also had a few quirks, like holding his breath during races and not being the most enthusiastic during morning workouts. So the odds were stacked against him at +10,800. Even the owner, Gary West, said after the race that it was crazy to put Rockamundo in the race at all!

But here’s where the story takes an exciting turn! Despite the odds stacked against him, Rockamundo stunned everyone with a blazing 5-furlong workout under jockey Calvin Borel. The two formed an instant connection and Borel decided to keep Rockamundo close to the pacesetter, Foxtrail, throughout the race.

As they approached the stretch, Foxtrail veered slightly off the trail, creating a narrow opening for Rockamundo and Borel. They wasted no time and swiftly maneuvered through the gap, leaving everyone in awe. Against all odds, Rockamundo crossed the finish line as the triumphant winner, defying expectations.

3. Jim Dandy (1930)

Despite being considered the presumptive loser with daunting odds of +10,000, Jim Dandy proved that in horse racing, anything is possible.

The Travers Stakes, known as the “Travers Mid-Summer Derby,” has a long and prestigious history dating back to 1864, making it the oldest race for 3-year-old thoroughbreds in the country. In 1930, it was the race everyone wanted to see, with a crowd estimated to be between 30,000 and 50,000 people. And guess what? It was one of the first races ever broadcast live on radio! Even then-Governor of New York, Franklin D. Roosevelt, was captivated and watched the race from the infield.

In the 1930 Travers Stakes, the competition at the starting gate was fierce. Gallant Fox, the Triple Crown winner, was the favorite, while Whichone was seen as his main rival. Sun Falcon (+4,000 odds) had moderate success, but Jim Dandy entered the race as a significant underdog with odds of +10,000. His recent performances had been lackluster, with only one moneyed finish in 10 starts.

But it’s no secret that all types of horse racing can be full of surprises! Against all expectations, Jim Dandy showcased his true potential that day, defying the odds and capturing the hearts of spectators. This remarkable underdog story reminds us that in the world of horse racing, anything can happen — even the least likely contenders can rise to greatness.

4. Donerail (1913)

Let’s now introduce the remarkable pair responsible for the historic triumph of Donerail, the greatest longshot winner in Triple Crown history: the esteemed jockey Roscoe Goose and the equally esteemed owner Thomas P. Hayes. 

In 1913, Donerail defied expectations as the underdog in the inaugural race that permitted working-class individuals to place bets with a minimum stake of $2. Initially hesitant to enter due to financial considerations, Hayes was eventually convinced by jockey Roscoe Goose’s persuasive arguments. 

To further complicate matters, Donerail had to traverse a 3-mile journey through Louisville on the day of the race due to overcrowded stables. Against all odds (a staggering +9,100,) their determination yielded an extraordinary outcome in front of an unprecedented audience of 30,000 spectators, resulting in a winner’s purse of $6,600, which holds the equivalent value of approximately $20,000 in today’s currency.

5. Rich Strike (2022)

In the world of horse racing, unexpected triumphs often create the most thrilling moments. The 2022 Kentucky Derby witnessed one such story with Rich Strike’s victory. Against odds of +8,000, guided by jockey Sonny Leon and owned by RED-TR Racing, Rich Strike displayed unwavering determination. From 18th place, he overtook four horses, delivering a breathtaking surge in the stretch run and securing the prestigious Kentucky Derby crown.

The victory was especially sweet, considering the humble origins of Rich Strike. Just eight months earlier, trainer Eric Reed had purchased him for a mere $30,000. Little did anyone know that this underdog would deliver an astonishing return on investment.

The triumph at the Kentucky Derby not only earned Rich Strike a place in the winner’s circle, but also a remarkable winner’s purse of $1.86 million. The sheer magnitude of the achievement left even Reed, watching from the stables, stunned and overwhelmed with emotion.

6. Sarava (2002)

Jockey Edgar Prado and owner New Phoenix Stable found themselves at the center of a historic upset in 2002 when Sarava won the Belmont Stakes. 

War Emblem, after winning the Kentucky Derby and Preakness Stakes, appeared unstoppable on his quest for the Triple Crown at the Belmont Stakes. However, it was Sarava who defied the odds, shocking everyone with a victory at +7,000 odds. 

Sarava’s inconsistent performances in England and the US hadn’t garnered much attention from the oddsmakers and touts, breaking from the gate at +7,000 odds. Sarava patiently stayed in the middle of the pack for the first mile. As the home stretch approached, he surged forward, crossing the finish line half a length ahead of Medaglia d’Oro and leaving the highly favored War Emblem far behind.

Sarava’s triumph in front of a record-breaking crowd of 103,000 fans remains one of the highlights of his career, defying expectations and making his mark in racing history.

7. Country House (2011)

Finally, let’s talk about an unforgettable moment in Kentucky Derby history featuring Country House, with odds of +6,500 and guided by jockey Flavien Pratt. Owned by J.V. Shields Jr., E.J.M. McFadden Jr. and L.N.J Foxwoods, Country House’s victory took a surprising turn.

In a twist of events, Maximum Security initially crossed the finish line first. However, Country House’s jockey, Flavien Pratt, recognized the interference caused by Maximum Security and promptly reported it. This led to a historic decision to overturn the win, crowning Country House as the official victor.

Unfortunately, Country House’s triumph was short-lived. The horse fell ill with a virus, preventing him from competing in the Preakness Stakes. This marked the first time since 1996 that the Kentucky Derby winner did not participate in the Preakness. Due to the ailment, Country House retired from racing and did not compete again.

Reputation Wins the Day

In most cases, the favorites in horse racing tend to live up to their reputation, meaning the winner is often a contender who was expected to perform well. While upsets can happen, it’s not common for the winner to come completely out of nowhere when the frontrunner falls short. That’s part of what makes these upsets unique and memorable for all of us.

American bettors’ passion for betting on horse races adds to the excitement and thrill of horse racing. If you enjoy horse racing betting, you’ll be delighted to know that leading online sportsbooks like NYRA Bets provide excellent opportunities for online sports betting. 

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Our BetMGM editors and authors are sports experts with a wealth of knowledge of the sports industry at all levels. Their coverage includes sports news, previews and predictions, fun facts, and betting.

Our BetMGM editors and authors are sports experts with a wealth of knowledge of the sports industry at all levels. Their coverage includes sports news, previews and predictions, fun facts, and betting.