The Biggest Horse Racing Upsets Throughout History

There’s nothing quite like the thrill of the biggest horse racing upsets. Just when everything seems certain, the roar of the crowd rises, and a rank outsider bursts through the field to snatch victory from the favourites. These moments are more than surprising, they’re legendary. They leave jaws on the floor, betting slips torn to pieces, and become stories passed down through generations of punters and fans.

In horse racing, unpredictability is part of the charm. While many follow the form, the odds, and the favourites, it’s the outliers, the 70-1s, the longshots, the no-hopers, that sometimes steal the show. These unexpected champions have delivered some of the biggest horse racing upsets in history.

Here Are Some of The Biggest Horse Racing Upsets Throughout History

Upset Beats Man o’ War: 1919 Sanford Memorial (Odds: 8-1)

You know you’ve made history when your name becomes the very definition of a racing shock. That’s exactly what happened in 1919 when Upset defeated the then-undefeated legend Man o’ War at the Sanford Memorial. With just one loss in his career, Man o’ War was expected to coast through this race, but a troubled start and tactical missteps opened the door for the underdog to clinch a historic victory.

It remains one of the biggest racing shocks of all time, and yes, the term “upset” in sports was already in use, but this race gave it unforgettable context.

Donerail Defies Logic: 1913 Kentucky Derby (Odds: 91-1)

Long before analytics and algorithms, Donerail’s win in the 1913 Kentucky Derby was a punter’s dream…or nightmare, depending on your bet. With staggering odds of 91-1, Donerail galloped to victory in front of over 50,000 stunned spectators, marking the biggest Kentucky Derby upset still on record.
Even today, bettors looking for the biggest Grand National upset or Derby shock refer to Donerail’s stunning run as a reminder that anything is possible.

Wild Again Takes Inaugural Breeders’ Cup:1984 (Odds: 31-1)

The first-ever Breeders’ Cup Classic was meant to be a showcase for the sport’s finest. Instead, it turned into a brawl of epic proportions, with longshot Wild Again coming out on top. With an aggressive ride, a wild stretch duel, and a controversial inquiry that lasted 10 minutes, Wild Again’s name lived up to the race. He delivered one of the most chaotic and dramatic finishes the sport has seen.

It was the kind of win that captured everything great about racing: unpredictability, passion, and a bit of madness.

Arcangues Shocks the World: 1993 Breeders’ Cup Classic (Odds: 133-1)

No list of the biggest horse racing upsets would be complete without Arcangues. A French turf horse making his first start on dirt, Arcangues went off at odds of 133-1, making him the longest-priced winner in Breeders’ Cup history. Almost no one saw it coming, and the stunned silence followed by gasps of disbelief still echoes through the halls of racing lore.

This wasn’t just a betting shock, it was a global headline.

Sarava Stuns Belmont: 2002 Belmont Stakes (Odds: 70-1)

When War Emblem entered the 2002 Belmont Stakes chasing a Triple Crown, the world watched in anticipation. What they didn’t expect was Sarava, a little-known colt at 70-1 odds, to crash the party and crush the dream. With one surge down the stretch, he rewrote the narrative. and earned a spot in racing’s hall of upsets.

Belmont has always been a graveyard for favourites, but Sarava’s victory was particularly haunting.

Keen Ice Halts a Legend: 2015 Travers Stakes (Odds: 16-1)

American Pharoah had already claimed the Triple Crown ending a 37-year drought and looked unstoppable heading into the Travers Stakes. But in a race few expected to be competitive, Keen Ice, a 16-1 outsider, surged past in the final furlong to hand the champion his only defeat that year.

It was a reminder that even legends are mortal, and the underdog always has a chance.

Why We Love a Longshot

Whether it’s the Derby, the Grand National, or the Breeders’ Cup, these unlikely victories remind us that in racing, nothing is guaranteed. The biggest racing shocks carry more than monetary stakes, they carry emotion, legacy, and a sense of wonder. These are the races punters talk about for decades, the stories we share over a pint or in the stands, and the moments that make racing unforgettable.

Inspired by these incredible feats? Who knows, maybe the next big upset is just around the corner. Read the latest horse racing news and previews. Place your bets now on TangoBet.

Whether you’re backing the favourite or betting on a bold outsider, TangoBet puts you at the heart of the action. After all, sometimes the best wins come from the back of the pack.