Five biggest upsets in horse betting

| February 15, 2016
Long-shot Prince of Penzance won Australia's greatest race.

Long-shot Prince of Penzance won Australia’s greatest race.

Upsets and surprise winners are of course a part of every sport, and also part of the reason why so many of us tune in to watch. But the excitement of a surprise underdog victory is always kicked up a notch in horse racing, a sport that has had gambling ties as far as back as you want to trace. Regardless of if you understand the nuances of the sport or not, few things are more exciting than putting $2 on a long shot and watching him outpace the field down the final stretch in a massive (and lucrative) upset.

Here’s five of the biggest (and most exciting) horse racing betting upsets ever.

1919 Sanford Stakes–Upset

Man O’ War is widely considered one of the greatest race horses of all time. Winning 20 of 21 career races, he would go on to sire or otherwise appear in the bloodline of other all-time great horses such as War Admiral, Seabiscuit, and American Pharoah. That one blemish on his record came as a two-year old in the seventh running of the Sanford Memorial Stakes in Saratoga Springs, New York.

According to news reports, the race began before all of the horses, including Man O’ War, were even set at the gate. The legendary chestnut thoroughbred would overcome the poor start to lose by a nose to the appropriately-named Upset, and it’s widely accepted that if the race were 20 feet longer Man O’ War would have won. ‘Man’ would go on to win every race the rest of his career, including six times against the horse that beat him in Saratoga. Despite common lore, however, the word ‘upset’ was already being used to describe a winning underdog decades before this betting miracle took place.

1989 Epsom Derby–Terimon

One of the biggest upsets in horse racing history didn’t come from a winning horse at all. Instead, it was the horse that finished in second place that is most remembered from the 1989 edition of the Epsom Derby, the UK’s richest horse race.

Despite being the most experienced horse in the field, Terminon was pegged at 500-1 odds of winning in the nearly 2,500m race. As favorite Nashwan pulled away in the final stretch, Terimon made a late push to take second, paying out punters that had backed him “each way” (meaning either place or show) 125-1. Perhaps the only person not surprised by the result was trainer Clive Brittain: “We didn’t think we could beat Nashwan, but I put him there to be placed and I told his owner that he would be placed – and we were.”

1993 Breeder’s Cup Classic–Arcangues

Due to the sheer caliber of horses that compete in it every year, the Breeder’s Cup Classic has gained a reputation for being an incredibly hard race to forecast. A big reason for this reputation is due to what happened in the 1993 edition of the race, which saw its first foreign-based winner crowned.

Only having ridden on grass and in Europe prior to the 2,000m race, the French chestnut Arcangues was rightly given 133-1 odds. This might have also had to do with the fact that on board this thoroughbred would be last-minute substitute jockey Jerry Bailey, who reportedly couldn’t even understand the instructions of his French trainer or pronounce the name of the horse.

All of that makes what happened next even more improbable, when Arcangues overcame favorite Bertrando in the final furlong to cement his place in horse racing history and pay out faithful (or foolish) bettors $269.20 on a $2 bet, still the largest payoff in Cup history.

2005 Kentucky Derby–Giacomo

Eventual American Thoroughbred Hall of Famer Holy Bull couldn’t do any better than 12th in the 1994 Kentucky Derby despite being both the odds on favorite and unbeaten up to that point in his career. So vindication was somewhat achieved when his offspring Giacomo would go on to be one of the biggest underdog winners in the history of the race just 11 years later.

Bettors were stunned as four horses ran side-by-side down the final stretch, a mass that included the top two favorites in Bellamy Road and Afleet Alex (who would go on to win the Preakness and the Belmont) against two of the field’s biggest underdogs in Giacomo and Closing Argument. The 50-1 Giacomo would eventually prevail in the final furlongs, in what was then the second-biggest long shot victory ever in the 130+ year history of the race. Prior to his victory in the Run for the Roses, Giacomo’s only victory was in his maiden.

Online gambling, especially horse racing, now remains popular across the world, offering a far easier way of placing bets than the old school bookies at the racetracks. Options for Australian punters are plentiful and many offer great promotions like free bet offers or welcome bonuses.

2015 Melbourne Cup–Prince of Penzance

The winning horse of Australia’s most prestigious thoroughbred race in 2015 was notable beyond just the fact that he was ridden by the first female jockey to ever win the Cup. Against a field of international winners, Prince of Penzance, an 100-1 outsider in the 24-horse field, held his position near the front of the pack throughout the race,  eventually taking the lead and the Cup in the final 100 meters.

Despite overcoming odds that would tie two other horses for the largest victorious long shots in the Cup’s long history, several punters made out like bandits according to one customer in particular walked away from the window with about $170,000 after cashing in a series of bets on the horse that was given little attention before the start of the race.

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