The Biggest Underdog Wins In Betting History

October 13, 2020
The Biggest Underdog Wins In Betting History

There are a plethora reasons why we like to place bets. We do it to make life a bit more exciting when there is a boring match up, such as Fulham versus Crystal Palace. If we are honest, though, then more often or not, we do it because we would like to win some money. It is why so few of us can resist wagers with long odds, although we know they do not have much of a chance of winning. The main factor of winning big on an underdog is choosing the right bookmaker to place you bet at; check out more reviews on the UK’s best bookmakers to find where offers the most generous odds.

That is why I have decided to take a look at some of the biggest underdogs that have ever won against all of the odds, which, if we’d had a bet on, we would be over the moon about. Just remember, it is as likely to happen as Leicester winning the Premier League.

Leicester City Win the Premier League – 5000/1

It is impossible to talk about underdog stories without giving the top spot to Leicester City and their Premier League football title win in 2016.

The Prime Minister becoming the Aston Villa manager, Elvis Presley being found alive, and the Queen recording a Christmas number one song were things that the bookmakers believed were more likely to happen than Leicester winning the top-tier title in the 2015-2016 season. A select few of supporters managed to back the bet at 5000/1, making it a bet with some of the longest odds ever to become a winner.

Boris Becker Wins Wimbledon – 11/1

This is an example of when the bookmakers’ odds do not necessarily reflect just how much of an underdog the winner of a given event was. Since seeding began at Wimbledon in 1927, no one had won the tournament as an unseeded player. In 1985, there were only sixteen seeds. So seventeen-year-old Becker, who was ranked twentieth in the world at the time, entered the tournament unfancied. Although he had won the tournament at Queen’s Tennis Club just a couple of weeks before.

His win at Queen’s aside, it is not overly surprising that small group of people expected Becker to win. The German national was so young that the winner of the Boys’ Singles event, Leonardo LaValle, was a couple of months older. He also had a fierce run through to the final, having to take down sixteenth seed Tim Mayotte in the fourth round, the fifth seed Anders Järryd in the semis, and then went up against the vastly more experienced Kevin Curren. The latter was seeded eighth in the final. Big names, such as John McEnroe, Ivan Lendl, Jimmy Connors, and Pat Cash, were supposed to win the tournament, not a youngster from West Germany. Not entirely on the Leicester City level of surprise, but worthy of a mention.

Sanford Memorial Upset – 100/1

There is something delightfully appropriate about one of the competitors on this list being called ‘Upset.’ That, of course, was the 100/1 underdog that won the Sanford Memorial horse race in 1919. Man o’ War was considered to be one of the best racehorses of all time. The American thoroughbred had not lost a race when he was made the bookmakers’ favourite ahead of the Sanford Memorial Stakes in 1919. At the time, the racecourse did not have starting gates, with the horses expected to circle around and line up before the race began.

What happened next remains under dispute, with some claiming that the favourite, Man o’ War, had its back to the field as the webbing went up and the race got underway. Whatever the truth, he endured a torrid start and never recovered. Partly that was because of the mix-up at the start of the race, partly it was because of poor riding from the jockey who put him in a position to be boxed by other competitors. Irrespective, the significant favourite lost out by a neck to a horse that he had given up fifteen pounds to, with the race leading to the Saratoga course earning the nickname the ‘Graveyard of Champions.’ The winning horse, of course, had the appropriate name of Upset.

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