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Biggest Sports Upsets in History | Infographic

Watching sports is fun because a lot of things can happen in both a match and a sports league. While many people will be content with thinking that the favourites will always win, diehard sports fans will always want their teams to win even if they aren’t the favourites. Betting on the underdogs winning is exciting to do since something unusual will take place, and those who did place bets on a sportsbook can potentially win big.

One of the biggest upsets in sports history that also led to some of the biggest futures bet wins in betting history is when Leicester City won the 2015/16 English Premier League. Apart from Leicester, more upsets in sports history occurred throughout the years. These upsets should be able to convince bettors not to just bet on favourites every time.

Biggest Sports Upsets in History

Buster Douglas Keeps Mike Tyson from Fighting Evander Holyfield

Currently the biggest upset in heavyweight boxing history, Buster Douglas managed to beat Mike Tyson in 1990. Mike Tyson was the undefeated and undisputed heavyweight champion of the world and fought the challenger Buster Douglas who was the underdog with odds of 42/1 or 43.00 in SG odds.

Buster Douglas was supposed to be a warm-up for Tyson’s match with Evander Holyfield, but Tyson was unexpectedly beaten. This outcome was so unexpected that two HBO analysts even said that the fight would be over within 90 seconds, only for it to end with a knockout blow in the 10th round.

Mike Tyson struggled to find his rhythm, and Douglas made a strong start while his confidence continuously grew. Six months after Douglas won the crown, Holyfield would snatch the title through a KO.

Leicester City Wins the 2015/16 Premier League

We already mentioned Leicester City before as pulling off a big upset. Their win also resulted in UK bookmakers paying out £20 million to bettors. Leicester City’s initial outright odds of winning the season was 5,000/1 or 5,001.00, making it a no-brainer to avoid it.

One bettor placed a £5 bet and won £20,000 while the odds were still 5,000/1. Other bettors, including the one who won £200,000, placed their bets when the odds lowered to 2,000/1, and others when the odds went further down to 1,000/1 and onwards.

Leicester City owed its victory to Jamie Vardy, Riyad Mahrez, and N’Golo Kante. Leicester finished the season with 10 points clear at the top of the EPL table.

Emma Raducanu Wins the 2021 US Open

Emma Raducanu, aged 18, already made a name of herself at Wimbledon 2021, but it’s still not enough to justify making her a favourite in the US Open. Her odds of winning were 400/1 or 401.00, but she took the tennis world by storm after winning.

Raducanu’ world ranking was 150 before the 2021 US Open, and she won the £2 million prize money by blowing away every opponent she faced. She was also the first player to win a slam at only the second attempt, with the previous record being winning a slam in the fourth attempt by both Monica Seles and Bianca Andreescu.

Raducanu’s win at the 2021 US Open is not only one of the biggest upsets in tennis history but also in the entirety of women’s sports.

Chelsea Beats Bayern Munich in the 2011/12 Champions League final

Chelsea F.C. was the big underdog in the finals match of the 2011/2012 Champions League against Bayern Munich. The finals were also held in Bayern Munich’s home stadium in Germany, making them the home team with a significant advantage over the away team Chelsea.

Both Chelsea and Bayern Munich scored at least an upset each in the Champions League. Chelsea scored an upset against Barcelona in Spain, while Bayern Munich scored an upset against Real Madrid. During the finals, another upset happened with Chelsea winning against Bayern Munich.

Chelsea’s odds of winning, according to Odds Shark, was 4.33, which is somewhat high for a single match and something that can be taken advantage of by avid fans who want to show their support by staking high. Bayern Munich was the obvious favourite with odds of 1.80, and the odds alone should be enough to convince bettors to back them up.

Other Big Upsets

The four upsets mentioned above are barely scratching the surface as there should be multiple instances of underdogs making unbelievable upsets that both changed sporting history and made lucky bettors rich. There should be at least 50 big upsets in sports history, with more happening today since there are tons of sports events held each year.

Some of the other big upsets in history include the following:

  • Appalachian State Beats #5 Michigan and Ends its National Title Hopes In the First Week
  • US National Hockey Time Winning the 1980 Olympics Miracle On Ice Against the Soviet National Team
  • New York Giants Ruin the New England Patriots Hopes for a 19-0 Record in the Super Bowl XLII
  • New York Jets beat Baltimore Colts in 1969
  • Greece Wins Euro 2004 Without a Single Star Player
  • Rulon Gardner wins Olympic gold medal over Aleksandr Karelin


Upsets may be rare, but it’s undeniable that they’re not as rare as people might think. Plenty of underdogs have already pulled off big upsets in the past, and several bettors have already managed to capitalize on them. If bettors bet on underdogs more, then they’ll have more chances of winning big should a particular athlete or sports team defy the odds. Anything can happen in a match, so backing the underdogs still remains a good bet.

When betting on sports, bettors should register in a reputable SG bet casino with access to reputable sportsbooks like CMDBet and M8Bet. Register at CM2Bet to get started betting on different sports events today.

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