Ranking the 10 Craziest Wins in Horse Racing History

By J.W. Paine in Horse Racing
| July 9, 2022 11:16 am PDT
Horse Racing Gate with horses

Nothing livens up a day at the horse races better than a good upset. The problem is that the biggest races—the Kentucky Derby, the Breeders’ Cup Classic, the Belmont Stakes—are decided by the top horses in the world.


Watching a competitor beat long odds is far more exciting than watching a race between a handful of equally-matched horses. Yet, it’s the crazy win—the one nobody saw coming—that keeps many of us coming back to the best horse racing betting apps.

Some of these horse racing wins are big crazy, while some – like the one I’ve ranked #10 on the crazy scale – are slightly more subtle. I’ve got you covered if you came here looking for some of the most shocking wins in horse racing history.

I rank the ten craziest below.

10. Beating the G.O.A.T.

These days, the Whitney Stakes is a Grade I stakes race, but in 1973 it was called the Whitney Handicap and had just been bumped up to Grade II. It was a great race to provide Secretariat—a recent winner of the Kentucky Derby—with another showcase for his amazing running abilities.

Run first in 1928 as a 1-1/4 mile handicap; since 1955, the Whitney has been run on the dirt track for nine furlongs (1-1/8 miles). Among Secretariat’s competitors in 1973 handicap was Onion, a game three-year-old chestnut gelding who under any other circumstances would probably have been considered a favorite by the oddsmakers.

And as it was, even against Secretariat—the horse who won the Kentucky Derby and set the still-standing time for that race (1:59.4)—Onion’s odds were 9/2. Not favorite-level odds, but Onion was no longshot here, either.

In fact, at the break, Onion took the lead of this short field of five and left Secretariat behind to fight it out with the also-rans. Of course, Secretariat was well-known for running faster the deeper into the race he got, and sure enough, as they rounded the final turn, Secretariat was fighting for second place. At one point, the and Onion were neck and neck, but Onion pulled ahead in the final yards and crossed the finish line a full length ahead of Secretariat.

This was an upset victory, not because Onion was not considered good enough, but rather that Secretariat, in 1973, seemed unbeatable.

9. Happy—And Just a Bit Surprised—to Be Here

The three-year-old colt Animal Kingdom made it into the 2011 Kentucky Derby with little to brag about. He’d broken his maiden on his second attempt, then after a second-place finish in an allowance race, managed to win the Spiral Stakes (now known as the Jeff Ruby Steaks), a Grade III dirt track run.

That was j-u-s-t enough to give Animal Kingdom a ticket to the Kentucky Derby, but he entered the starting gate at Churchill Downs at 21-1. To say the oddsmakers were unimpressed and this classifies as one of the most shocking horse racing wins ever would be an understatement.

This was to be one of Animal Kingdom’s first races on the dirt track; most of his other runs were either turf or synthetic surfaces. At the break, Animal Kingdom was in the last position in the 11-horse field, and until the second turn, he remained there.

As the runners entered the second turn, it was obvious Animal Kingdom was rope-a-doping the others as he moved ahead of one horse after another. As the horses came out of the second turn, Animal Kingdom had taken the lead.

Decisive Moment battled him briefly but eventually lagged, and Animal Kingdom won the Spiral Stakes by two lengths.

8. A Slingshot to Fame

An import from Great Britain, Sheikh Albadou was not expected to finish in the money in the 1991 Breeders’ Cup Sprint.

No surprise. He’d finished eighth in a field of eleven at Newmarket Racecourse for his initial maiden attempt. He did manage to win his second attempt in 1992 at Pontefract Racecourse. He then saw limited success in some longer runs, performing better at the shorter sprints.

But that was in England, and Gulfstream Park in Florida is a long way from jolly olde. The odds that Sheikh Albadou was very skeptical 26-1.

Shortly after the break, Sheikh Albadou was seventh from the lead in a ten-horse field. He remained among the also-rans until the final turn when he used something like a centrifugal force to slingshot around the outside to challenge for a money position. In the final furlong, he exceeded those expectations and took a solid lead, hitting the wire with a three-length lead.

7. If You Only Win Once, Make it a Good One


The year was 1925, and the scene was Pimlico Race Course in Baltimore, Maryland. It’s the running of the second jewel of thoroughbred horse racing’s Triple Crown—the Preakness Stakes. This will be the first time the Preakness is run at its current distance of 9-1/2 furlongs (earlier Preakness races were run at various slightly shorter distances).

Among the competitors is a three-year-old colt named Coventry, who had yet to win a single race. In his brief career, Coventry only entered five races. And managed to win only one.

He picked a heck of a time to get that elusive victory, though, choosing the 1925 Preakness Stakes.

Oddsmakers gave him 28-1 against winning the Preakness.
When the gates burst open at Pimlico, Coventry quickly settled mid-pack, apparently prepared to fulfill all the oddsmakers’ doubts.

But late in the race, he discovered ambition. He fought his way past one horse after another until he finally took the lead from the heavily-favored Backbone.

One can only hope he enjoyed the winner’s circle because it would be his only visit. Coventry had bowed a tendon during the Preakness, and in his next race—the Withers Stakes—he broke down and was retired to stud.

6. Close But No Cigar

In 1996, everybody figured the winner of the annual Pacific Classic Stakes (Grade I) would be the thoroughbred that won his last 16 races: the six-year-old Cigar.

It was a tight six-horse field that entered the starting gate for the Pacific Classic, and the odds were long on five of the entries. Cigar, of course, was the 1-9 favorite. A two-dollar bet on him to win would pay a juicy $2.20. One of the least likely to win was the five-year-old Dare And Go, who the oddsmakers put at 39-1.

And at the break, it looked like Cigar fans were going to be taking that twenty cents to the bank, with Cigar in the lead of the six-horse field. For much of the race, Cigar battled two other frontrunners– Dramatic Gold and Siphon——and they managed to tire themselves out in the final furlongs, giving Dare And Go the opportunity to slip past the frontrunners and to cross the wire well ahead of them.

Cigar’s winning streak was at an end (he did finish second in this race, though, so… good effort!)

5. You Snooze, You Lose

Even in a twelve-horse field that included 2002 Kentucky Derby & Preakness Stakes winner War Emblem, Volponi should have started the 2002 Breeders’ Cup Classic with better odds that the longshot 44-1 he broke with.

After all, he’d campaigned hard—and successfully—at the graded stakes level, winning three of his four graded stakes runs leading up to the 2002 Classic.

Yeah, those 44-1 odds had to sting. Still, the longshot skepticism didn’t seem to phase either Volponi or his jockey, Jose Santos, as the pair settled in toward the back of the bus as the race progressed.

In the meantime, Medaglia d’Oro and War Emblem fought each other for the lead.

It wasn’t until the final turn that Volponi made his move—a mad dash on the inside that brought him into the lead just as the other frontrunners were finishing the turn and heading for home.

By the time he hit the wire, Volponi was a solid six lengths ahead of the second-place finisher, Medaglia d’Oro. And War Emblem? He finished in eighth place.

4. Look At All that Glorious Mud!

At 50-1, Mine That Bird wasn’t expected to do much at the 2009 Kentucky Derby except to pick up his participation trophy on his way home.

The competition in the 19-horse field was, as always, quite formidable, and the heavy rain the night before had left the track “sloppy.”

Mine That Bird had had some early success in listed stakes runs, but as the big KD neared, his performance was, shall we say, less than stellar.

And when the gates slammed open, and 19 Kentucky Derby hopefuls charged forward, Mine That Bird promptly took last place and clung to it like it was a birthright.

Oddly enough, another 50-1 longshot, Join in the Dance (also at 50-1), had been in the lead since the break, remaining there until Mine That Bird made his move at the final turn.

Up the inside, he came, and within seconds, Mine That Bird had usurped the other pretender and by the final furlong was widening his lead. He crossed the finish line 6-3/4 lengths ahead of the second-place finisher, Pioneer of the Nile.

While he came in second at the Preakness and ran third in the Belmont Stakes, Mine That Bid never won any of the nine races he started after the KD win. Maybe if they’d watered down the track a bit…

3. Day of the Longshots

Like the guy said, it’s an honor just to be nominated. That had to have been what Giacomo thought when he was guided into his chute at the starting gate for the 2005 Kentucky Derby. The bookies had him at 50-1, and he’d earned every one of those 50, failing to win anything before the KD than his second maiden attempt back in 2004.

Sweet dreams aren’t made of these.

Giacomo started the race in 18th place—a position he would hold for much of the run. It wasn’t until the final turn that he began easing closer to the frontrunners. In the final stretch, he charged into the lead, holding it and finishing in first place by half a length.

Interestingly, the 20-horse field included six horses running at even longer odds than Giacomo. Only one of those, Closing Argument (at 71/1), finished in the money—second, to be exact, half a length behind Giacomo.

During his career, Giacomo won only three races—his second maiden attempt in 2004, the 2005 Kentucky Derby, and the San Diego Handicap (Grade II) in 2006.

2. The Winner and Still Champion (Sort of)


Donnerail has the distinction of holding the record of longest odds to win the Kentucky Derby (91-1) for more than a century. He won the 1913 Kentucky Derby in a field of eight (reduced from 12 by late scratches).

At the time, even his owner, breeder, and trainer– Thomas P. Hayes—wasn’t convinced Donerail had it in him to win. “get a piece of the purse” is what Hayes told his jockey, Roscoe Goose.

But Goose had a plan. When the race began, he settled on the outside and stalked the frontrunners. And then, in the final stretch, Goose had Donerail kick in the afterburners, and between the two of them (but mostly Donerail, tbh), they managed to cross the wire first, just a half a length ahead of Ten Point, the favorite.

1. King Arcangues

The tenth running of the Breeders’ Cup Classic was in 1993 and was held for the second time at Santa Anita Park. Thirteen of the world’s best thoroughbreds lined up nervously behind their starting gates. Among them was Arcangues (pronounced “ar-KONG”), a five-year-old chestnut colt from France.

This would be his first race on American soil. Worse, he’d only raced on turf courses back home; this would be his first professional turn on a dirt track.

There are no reports of him sneering or mumbling insults about his stablemates, but the oddsmakers certainly weren’t shy about voicing their low opinions of his chances. When the Classic began, Arcangues’ odds were 133-1.

The favorite, Bertando, led the race from the start, holding first place long into the final stretch. Arcangues, on the other hand, struggled in the backfield around 11th and 12th place until the 3/4-mile mark when he surged into seventh place.

Not great, but better than 12th, right? Into the stretch, he poured it on, suddenly moving into second place, and then, in the final furlong, he took the lead from Bertrando and never looked back. He won the Classic by two lengths.

Which Horse Will Impress Us Next?

That does it for my top 10 most shocking horse racing wins. You could argue some in or some out, but there’s no denying this is one thrilling list of iconic horse racing finishes.

Nobody really knows about trying to project the next crazy longshot. It could be a 50-1 wannabe running her first allowance race at Del Mar. It could be an older campaigner with a long history of not quite making it who still has one win left in him.

One last thing: If the world of horse racing is still uncharted territory for you, we’ve blazed some trails for you to follow with our horse racing betting guide.

On the other hand, if you’re an old hand at betting on live sports, be sure to have a look at our best sports betting sites.

Good luck!



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