The Craziest Wins in Horse Racing History

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Jockeys riding on horses racing each other on a green grass track
BetMGM @BETMGM Jun 02, 2023, 11:47 AM

Let’s be real — there’s something truly magical when a total underdog defies low expectations. It’s those breathtaking victories, the ones that blindside us, that inject an unmatched level of excitement into the sport of horse racing and keep us hooked on horse racing betting, whether we place bets at the track or through the best online sports betting apps. 

Get ready to be blown away as we take you on an exhilarating journey through the top 10 craziest wins in United States’ horse racing history.

History of Horse Racing

If you feel up to tracing the origins of horse racing to its roots, you’ll end up going as far back as ancient, mythological times when horse racing was used to settle fights between powerful opponents. Organized horse racing as we know it began with King Charles II with the King’s Plates races. This could explain why horse racing is called the Sport of Kings. By the 18th century, the sport had moved away from entertaining only the nobles to something more public. 

The public appetite for horse racing came from the growing appetite for winning, which inevitably leads to attempts at cheating. As interest in the sport grew, classic races like the St. Leger in 1776, the Oaks in 1779 and the Epsom Derby in 1780 were created. Nowadays, some of the biggest races to look forward to include, but aren’t limited to, the Epsom Derby, Prix de l’Arc de Triomphe, the Melbourne Cup, the Kentucky Derby and the Dubai World Cup. 

Now, let’s jump straight into those crazy stories.

10. The Heart-Stopping Arazi (1991)

Arazi’s sensational triumph in the 1991 Breeders’ Cup Juvenile at Churchill Downs remains etched in Thoroughbred racing lore as one of the most awe-inspiring displays of talent and determination.

Hailing from France with an impressive record of six consecutive Group wins, this Kentucky-bred prodigy made his much-anticipated debut on American soil in the Juvenile.

Arazi trailed behind in the race but delivered a jaw-dropping performance by unleashing a late burst of speed, effortlessly overtaking his rivals and crossing the finish line an astonishing five lengths ahead.

9. The Victory of Rags to Riches (2007)

Rags to Riches’ historic triumph in the 2007 Belmont Stakes solidified her place in history as one of the few fillies to conquer the challenging race, breaking a century-long drought for filly winners. 

Horse racing is mostly dominated by males — equine runners and human trainers and riders — but this victory shows that female trainers, runners and riders shouldn’t be overlooked.

As the starting gates opened, Rags to Riches stumbled slightly but quickly regained her footing. Jockey John Velazquez expertly guided her through the pack, maneuvering past rivals with calculated precision. 

The race unfolded with breathtaking intensity as Rags to Riches engaged in a thrilling duel with the formidable Curlin, a colt who had already made a name for himself on the racing circuit. The two competitors matched each other stride for stride. In the final stretch, Rags to Riches found an extra gear and crossed the finish line first, by a head.

This victory made way for other filly winners and delivered an exhilarating showdown against Preakness winner Curlin. 

8. Sheikh the Underdog (1991)

Sheikh Albadou, a British import, defied expectations in the 1991 Breeders’ Cup Sprint. With skeptical odds of +2,600, he trailed the pack until the final turn. 

Suddenly, he unleashed a burst of speed, surging around the outside with slingshot-like force. Exceeding all predictions, Sheikh Albadou seized a commanding lead in the final furlong, crossing the finish line with an impressive three-length advantage.

This underdog’s remarkable victory stands as a testament to the thrilling unpredictability of horse racing, showcasing the extraordinary potential for triumph against formidable odds.

7. Coventry’s Famous Shot at History (1925)

In 1925, the Preakness Stakes at Pimlico Race Course in Baltimore made history by running at its current distance of 9½ furlongs for the first time, adding an extra level of excitement.

Among the bustling crowd of spirited contenders, there emerged Coventry, a three-year-old colt yearning to savor the thrill of victory. With a modest record of just five races and a solitary win, Coventry faced a daunting task ahead, with skeptics casting doubt upon his prospects.

Coventry started the race in the middle of the pack. Still, with unwavering determination, he surged forward, overtaking rivals and ultimately seizing the lead from the heavily-favored Backbone in a thrilling display of skill and determination.

6. Dare And Go Dreamed Big (1996)

In 1996, the annual Pacific Classic Stakes (Grade I) witnessed the remarkable presence of Cigar, a six-year-old thoroughbred with an astounding 16-race winning streak. As the clear favorite with odds of -10,000, Cigar stood out among the competitors, including the underdog Dare And Go, facing longer odds at +3,900.

Cigar started the race as the frontrunner, but as the competition heated up, Dramatic Gold and Siphon challenged him. However, in a stunning twist, it was Dare And Go who capitalized on their fatigue and unleashed a burst of speed to secure an unexpected victory, leaving spectators in awe of the thrilling upset.

5. The Battle of the Ages: Affirmed and Alydar (1978)

The 1978 Belmont Stakes showcased one of the greatest rivalries in horse racing history between Affirmed and Alydar. Having already triumphed in the Kentucky Derby and Preakness Stakes, Affirmed faced his unyielding shadow, Alydar, in the ultimate showdown. 

Neck and neck throughout the race, the two legendary horses battled fiercely, captivating the crowd with their sheer determination. Affirmed surged ahead in an epic display of strength and resilience, securing victory and completing the Triple Crown.

The monumental duel between Affirmed and Alydar stands as a testament to their unmatched talent and the enduring spirit of competition in the world of horse racing.

4. Mind. That. Bird. (2009)

Mind That Bird’s astonishing victory in the 2009 Kentucky Derby defied the odds and etched a remarkable chapter in the history of horse racing. Overcoming +5,000 odds, Mind That Bird surged from last place with incredible resilience, setting records as the longest-odds winner in 85 years and achieving the largest lead in 60 years, leaving spectators astounded by his extraordinary performance.

In the tapestry of the most exciting two minutes in sport, Mine That Bird solidified his place as the second greatest long shot ever to seize victory, second only to the incredible Donerail, who triumphed at odds of +9,100 in the 1913 edition.

Mind That Bird, ridden by jockey Calvin Borel, ran at the back of the field of 19 horses until the final turn, at which point he tapped into a reservoir of strength and determination. 

With each stride, he overtook rival after rival and finished 6¾ lengths ahead of second-place Pioneer of the Nile.

3. Long Shot Donerail (1913)

Against all expectations, Donnerail, with remarkable +9,100 odds, achieved a historic victory in the 1913 Kentucky Derby. Despite owner Thomas P. Hayes’ reservations, jockey Roscoe Goose defied instructions and guided Donnerail to a remarkable comeback.

With a burst of speed in the final stretch, Donnerail surpassed the frontrunners and crossed the finish line, defeating the favorite, Ten Point, by a narrow margin of half a length. This unexpected triumph etched Donnerail’s name in the annals of horse racing history, showcasing the unpredictable and exhilarating nature of the sport.

It was a victory that defied all odds and etched Donerail’s name into racing history as an unforgettable underdog who conquered the Kentucky Derby against remarkable adversity.

2. Santa Anita Triumph for Arcangues (1993)

In the 1993 Breeders’ Cup Classic at Santa Anita Park, Arcangues, a French chestnut colt, defied the odds and made history. Despite being a long shot of +13,300 odds, Arcangues showcased his determination and talent. Starting off in the backfield, he made a remarkable surge in the final stretch, moving from seventh to second place.

While the favorite, Bertrando, initially dominated the race, Arcangues languished in the backfield until the three-quarter-mile mark, where he mounted a remarkable surge and propelled himself into seventh place.

With an incredible burst of speed, he overtook the favorite, Bertrando, and secured a two-length victory.

1. Defeating Secretariat (1973)

In the 1973 edition of the Whitney Handicap, later known as the Whitney Stakes, Secretariat, the Kentucky Derby winner, faced off against Onion, a promising three-year-old chestnut gelding. Despite Secretariat’s impressive pedigree and record-breaking performances, Onion was given odds of +450, indicating a fair chance of success.

Onion took an early lead in the race, while Secretariat fought his way to second place, setting the stage for a thrilling duel between the two horses. Neck and neck, Secretariat and Onion fought on.

Onion’s unexpected triumph over Secretariat in the 1973 Whitney Handicap demonstrated the unpredictable nature of horse racing, highlighting Onion’s remarkable determination and resulting in a one-length victory. This memorable upset added a significant chapter to the race’s history, embodying the thrilling and unpredictable essence of the sport.

Bet on the Races With BetMGM

These 10 races are etched in horse racing history for their unforgettable moments, surprising outcomes and incredible displays of skill and determination, making them some of the craziest and most memorable races of all time. 

If you’re into sports betting, be sure to register with BetMGM to enjoy the best online sportsbooks and odds on horse racing with NYRA bets. And if you’d like to try your luck with other sports, you can bet online on football, basketball, hockey and a whole host of other sports, too.

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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.