Who was the most iconic surprise win in horse racing history?

Profile Picture: Nicolle Neulist

March 2nd, 2021

"That's why they run the race!"

It's an adage in horse racing for a reason.

We can take all the time we want handicapping races, but when the gates open, the race doesn't always go like it should.

For this week's poll, let's look back at some of racing's most shocking results. Then, you can decide the most iconic surprise in horse racing history.


In 2019, Country House lit the tote on fire after the Kentucky Derby (G1), at 65-1. However, he isn't the longest shot to win the Run for the Roses.

That honor goes to Donerail. He had yet to win during his three-year-old year in 1913, but he won twice at age two. The best he had done at three was a second-place finish in the Blue Grass S., but he picked the perfect time to remember how to win again.  He rallied down the lane at Churchill Downs, in time to beat favored Ten Point by a widening half-length. He set a Kentucky Derby record of 2:04 4/5.

After the race, owner/trainer Thomas Hayes stated he hadn't wagered on his horse. However, anyone who did cashed a colossal ticket. He paid 91-1.


The term "upset," as used for a surprising sports defeat, dates to at least 1877. We can't credit the horse Upset for coining that phrase, but did plenty to popularize it, when he won the 1919 Sanford S. at Saratoga, over the mighty Man o' War.

Man o' War, pne of the greatest horses of all time ran a valiant race. He started poorly, had traffic into the turn, and was forced wide into the lane. He came running into the lane, despite all the trouble, but fell just a neck short of 8-1 Upset. Contemporary reports call Man o' War the better horse on the day, since Upset got a perfect trip and carried 15 fewer pounds, but those are never enough to capture the trophy and the winner's share of the purse.

Man o' War never lost again, and Upset was the only horse ever to defeat the mighty chestnut.


Allen Jerkens built a reputation for training the longshots who defeated heavily favored superstars, but one name stands out in his roll of surprises.

Four-year-old Onion was fresh off of a 6 1/2-furlong allowance win at Saratoga, in track record time. Secretariat hadn't lost since the Wood Memorial (G1), more than three months before. In the meantime, he dominated the Triple Crown and won a procession at Arlington.

Jerkens wasn't sure about Secretariat's final work leading up to the Whitney (G2), and that was enough for him to take a shot with Onion. Onion cleared to the lead from the beginning. Secretariat drew closer down the backstretch, loomed inside around the far turn, and even brushed with Onion in upper stretch. Onion looked Secretariat in the eye, oblivious to the fact that he was staring down an all-time great.  In the final furlong, Onion edged clear outside of Secretariat and won by a length.

Though Secretariat was an all-time great and Onion never won a stakes again, Onion's success in the Whitney remains a testament to taking a shot with a horse in good form.


In the early 1990s in France, Arcangues was a nice turf horse. He won the Prix Eugene Adam (G2) at age three and and the Prix du Prince d'Orange (G3) at four, then finally notched his first Group 1 at age five, in the Prix d'Ispahan.

But could he run on dirt?

Going into the 1993 Breeders' Cup Classic (G1), the public either did not think so or thought the American dirt horses would be too good.

For most of the mile and a quarter around the Santa Anita main track, favored Bertrando had his way on the lead.

But Arcangues liked dirt enough.

He rallied up the inside around the far turn, split horses in upper stretch, and drew closer to Bertrando with every stride. In the final sixteenth, it was over. Bertrando settled for second, as Arcangues ran two lengths clear at odds of 133-1.

He remains the longest shot to ever win a Breeders' Cup race.

Dare and Go

He was the incomparable, the invincible, the unbeatable — Cigar.  But, no one told Dare and Go that.

Cigar entered the 1996 Pacific Classic (G1) on a 16-race win streak. He traveled all over the world that year, from Nad Al Sheba to Suffolk Downs, and had defeated all comers.

In the Pacific Classic, Cigar pressed right outside pacesetter Siphon, with Dramatic Gold just to his outside, the three on a sharp pace. Dare and Go, a 39-1 outsider in the field of six, waited along the fence. Through the far turn, Dramatic Gold gave in, but Dare and Go dared and went. He swallowed the gap, swung three wide into the lane, and passed the champion before they hit the furlong pole.

Dare and Go bounded 3 1/2 lengths clear of the champion to win the second Grade 1 of his career. As Trever Denman proclaimed as he crossed the wire, "this is one classy guy on his day."

Who was the most iconic suprise win in horse racing history?

Previous week's poll results

Looking back at last week's poll, Arlington Million (G1) winner The Pizza Man was not only a fan favorite during his racing career, but he still has a posse.

He won your vote for the best Illinois-bred of all time, with 40% of the vote.  It was a tight race for second, between Buck's Boy, Dust Commander, and Polar Expedition. Work All Week, once again, was The Pizza Man's under-the-radar stablemate.