Top 7 Biggest Upsets in Sports History


Upsets can occur in every sport. However, witnessing upsets of greater magnitude is quite rare. What is an upset anyway? An “upset” is an occurrence where an underdog defeats the favourite. The term upset is used both in Singapore horse racing and sports betting. Upsets happen due to many different reasons, including the following:

  • Overconfidence
  • Underestimating opponents
  • Carelessness
  • Having injured star players
  • Having the drive to win

Whatever the reason, it has proven that people love seeing a David vs. Goliath almost miracle win. And those kinds of matches are rare features in the sports world and don’t happen daily. Watching how the underdogs overpower sports powerhouses to the losing sides, snatching the victory just seconds away from the end of the match, makes peoples’ blood pumping from excitement. Here are some of the biggest upsets in sports history every sports fan should know.

Buster Douglas defeated Mike Tyson in 1990

During the late ’80s and ’90s, Mike Tyson was the undefeated and undisputed heavyweight champion of the world. Because of his ferociously strong punches and quick movements, he was feared and loved by many. In 1990, he went to fight with Buster Douglas, which was supposed to be his warmup before his big fight with Evander Holyfield.

Since Tyson was regarded as the best pound-for-pound boxer in the world, he was expected to have little to no struggle taking down his fellow American boxer, Buster Douglas, who had 42/1 or 43 odds at that time. Even the HBO analysts expected the fight to be over within 90 seconds.

However, to everyone’s surprise, Douglas made an excellent and robust start, immediately sending a message to Tyson that he’s not going down easily. The pound-for-pound champion then struggled to find his rhythm while Douglas grew confident. The knockout blow by Douglas landed in the 10th round, which made this match one of the greatest upsets in boxing history.

Apparently, the reason for Tyson’s defeat was because of a two-day party where he didn’t get to rest.

The USA win against England during the 1950 World Cup

During the 1950 world cup, the United States soccer team were underdogs with odds of 501 or 500/1 of winning the tournament. Although they did not manage to win the cup, they were able to beat England, which is still considered one of the greatest upsets in the history of football.

To call it a David and Goliath match might be an overstatement of the American’s abilities. They lost all their 7 matches by an aggregated score of 7-2 and were even described by their manager as “sheep ready to be slaughtered”.

However, the underdogs triumphed against one of the countries considered a powerhouse in football, England. This is all thanks to Joe Gaetjen’s goal strike and the goalkeeping of Frank Borghi.   

Leicester City wins the Premier League

It is known that the premiere league is usually dominated by world famous big clubs such as Manchester City, Liverpool, Chelsea and Manchester United. On the other hand, Leicester had gone for 123 years without winning any major titles until they entered the 2015-16 season with odds of 5001 or 5,000/1 to win the premier league title. They are big underdogs during the league, and it is clear that even the sportsbooks failed to predict their win.

They won thanks to their team effort and hunger to win. Thanks to the abilities of Jamie Vardy, the guile and trickery of Ryad Mahrez, and the prowess of N’Golo Kante. Leicester blew away the minds of football fans and the football world itself by finishing 10 points clear on top of the premier league table.

Liverpool’s excellent comeback victory against Barcelona

After a humbling defeat of 3-0 against the soccer powerhouse, Barcelona, during the first leg of the UEFA championship league, Liverpool made a massive comeback against Barcelona. But the win is somewhat hard fought due to the fact that three of their major scoring players are out of the game due to injuries that lead to a sub-team being fielded. The world was awed when Liverpool flipped the odds in their favour and left Lionel Messi and company bewildered by the 4-0 loss against the ‘Men in red.’

Roger Federer’s downfall against Juan Martin del Potro

For Tennis, the downfall of Roger Federer against Juan Martin del Potro is regarded as one of the greatest upsets in its sports history. In 2009, Roger Federer, one of the greatest tennis players of all time with multiple groundbreaking records, awards and trophies in his name, played against Juan Martin del Potro in a US Open final.

Since Federer was the reigning five-time defending champion during that time, many were convinced that he would sweep the whole competition again. However, Juan Martin del Potro managed to stun the world of tennis by forcing Federer into a fifth set. Ultimately overpowering him with a 6-2 win. That 2009 US Open finals title happened to be Juan Martin’s only major title in his career. However, it still was a match worth remembering.

Tipperary Tim, Grand National’s Biggest Upset

During the 1928 Grand National, thousands of fans watched as 42 horses set in line for the big race. Out of all the horses, almost only Tipperary Tim, a ten-year-old low-rank horse, received no cheering and made fans wonder why the horse was even in the race. Add the fact that Tipperary Tim was ridden by an amateur jockey, William Dutton, an assistant solicitor in Chester.

Tim received the odds of 101 or 100/1, way off compared to Master Billy, the favourite’s odds of 5/1 or 6. The fact that Tim and William had so little chance of winning made a friend say they’ll only succeed if all the horses fall. Little did that friend know that the words uttered would be prophetic as all the horses fall due to the heavy mist caused by a month-long heavy rain. Only Tipperary Tim, jockeyed by William Dutton, managed to navigate and gallop through the race. This unexpected win came down to be the biggest upset in horse racing history.

The 1990 Daytona 500 race

On February 18, 1990, the 32 running of the Daytona 500 was held at the international speedway in Daytona Beach, Florida. Dale Earnhardt, a renowned American stock-car racer, is about to win the Daytona 500 for the first time as he dominated the race until the last lap. It was certain that he would win the race at that condition and speed. However, Derrik Cope, back then was still an unknown racer, got his best finisher during the race. From the second place, he flew into first during the last lap when Earnhardt suddenly blew a tire. It took 3 hours to finish the race. Derrike Cope started from 12th place and won the race with an average speed of 165.761 MPH or 266.766 KM per hour with only three caution flags and 27 lead changes. Since that day, the 1990 Daytona 500 race was regarded as one of the biggest upsets in stock-car racing history.


Although very rare, huge upsets can happen in most sports. Most of them occur in a very unexpected moment, while only a few are predictable. Some are due to sheer luck, hunger for victory, incompetence and overconfidence. In sports betting, these upsets play a crucial part in winning bets. If not spotted early on, it might bring you losses. Make sure to review each team’s/player’s recent gameplay performance, injuries, lineups, and current standings to increase the chance of predicting or spotting a possible upset early on.

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