The 19 Biggest Upsets in Sporting History

When sports commentators exclaim that a series of events could not be written even by the most skilled script writers in Hollywood, they are usually exaggerating. Sometimes, though, sport produces moments that would indeed be deemed too far-fetched for fiction.

These are shocks that even betting sites never saw coming and their odds reflected that.

Everyone loves an underdog tale, and the thought that David can occasionally overcome Goliath is part of what continues to make sport one of the most popular pastimes on the planet.

Here are 19 of the greatest sporting upsets of all time, featuring improbable comebacks, unexpected one-off triumphs and more sustained surprises.

19. Wigan Shock Man City to win the 2013 FA Cup

While the FA Cup always provide us with unforgettable upsets, one of the biggest surprises of all time took place in 2013 as Wigan somehow beat a star-studded Manchester City outfit to lift the famous old cup. The Latics - led then by Roberto Martínez - enjoyed a blessed run to the decider, only having to beat one Premier League side (Everton in the quarter-final) along the way.

Man City had to defeat Chelsea to make the final and the mega-bucks club entered the game as massive 1.4 favourites to win with the best football betting sites. Wigan were having none of it though, and a Ben Watson header in injury time landed them, what remains, the only major honour in the club’s history.

18. Robin Soderling topples Rafael Nadal at the 2009 French Open

After 13 victories at the French Open from 17 attempts, there is little doubt that Rafael Nadal is the undisputed king of the clay. But, back in 2009, he looked utterly unstoppable on the courts of Roland-Garros, and was on a run of 31 straight wins from his first appearance in 2005. However, that was until he ran into Robin Soderling in the fourth round.

Court Philippe Chatrier was stunned as the big-serving Swede upset 49.0 odds on Betfair to take down Nadal in four sets (6-2, 7-6, 6-4, 7-6). The needle would continue between the pair throughout their careers, but Nadal had the last laugh beating Soderling in the 2010 French Open final.

17. Trevor Immelman Wins the 2008 Masters

In December 2007, South African Trevor Immelman underwent emergency surgery for the removal of a tumor on his abdomen. When he arrived at Augusta four months later, he was ranked 1,673 in the world, and was just relieved to be there taking part. Priced up at 151.0 with betting sites, nobody gave him a chance but he went on to prove the doubters wrong.

Immelman shot a 68 in the first round to go joint top of the leaderboard, repeated the feat in the second round and managed a 69 in the third. It meant he went into the final round two shots clear, and despite a 75, nobody came close, and he won the title finishing three shots ahead of second placed Tiger Woods who was one of the shortest priced favourites in Masters betting history at 2.5.

16. Anna Kiesenhofer Wins Road Race at Tokyo 2020

As a mathematician, one wonders what odds amateur cyclist Anna Kiesenhofer gave herself ahead of the women's road race at the 2020 Olympic Games.

Bookmakers put an enormous price of 501.0 on her head and she duly made a mockery of their knowledge.

Perhaps the bookies were too focussed on the history of the event – Austria had not won gold in this race since the 1896 Games – but it’s true to say Kiesenhofer was something of an unknown before her Tokyo heroics.

Being an amateur in a race scattered with pros, the 30-year-old wasn’t expected to be anywhere near the medal mix, although Kiesenhofer did spend a year as a pro in 2017. Perhaps that fact went unnoticed when traders were pricing up the market.

The Dutch riders – in particular Annemiek van Vleuten, who finished second – were expected to be the strongest but Kiesenhofer’s in-race decision-making saw her steal a march and sustain a lead. Her achievement made headlines worldwide and she was duly inundated with offers to return to professional cycling.

15. Gardner Stuns Karelin at Sydney Games

It may not get the attention of other sports, but Greco-Roman wrestling has been around since the Olympic Games first began. In the 2000 Summer Olympic Games, Alexander Karelin was heavily favoured to win the gold medal. In fact, it was considered almost a formality, as he had not lost a match in 13 years in international competition.

The Russian wrestler had already won three gold medals, nine world championships, and was European champion 12 times.

Another gold medal seemed destined for his mantle, but a “nobody” from Wyoming in the United States, Rulon Gardner, pulled off what is regarded as the biggest upset in Summer Olympics history. These days, this upset may not get the international recognition it deserves, but in 2000 it was one of the most talked about events in the world.

14. Patriots Defeat The ‘Greatest Show on Turf’

The Patriots lost one of the greatest upsets of all-time - more on which below - but were also victorious in one of the biggest upsets. The 2002 NFL Super Bowl seemed like an absolute lock for the St. Louis Rams, who were dubbed as the ‘Greatest Show on Turf’ and were favoured by 14 points in the game.

It was the first season with Tom Brady as the quarterback of the Patriots, and the team was expected to get trounced by the heavily favoured Rams. However, New England grounded the St. Louis offense for much of the game.

The Rams would battle back to tie the score at 17, but Brady led a two-minute drive that led to an Adam Vinatieri field-goal as time expired, giving New England a 20-17 victory against all odds.

13. Jeff Kidder The Biggest-Priced Cheltenham Winner in 31 years

Day 1 of the 2021 Cheltenham Festival was certainly a day to forget for the bookmakers after short-priced favourites Appreciate It, Shiskin, and Honeysuckle all won without a moment's sweat.

The Boodles Juvenile Handicap Hurdle provided the layers with some restbite after the unfancied Jeff Kidder sprang a stunning 81.0 surprise under Sean Flanagan to keep the 5.5 favourite Saint Sam at bay.

The Hallowed Crown gelding was the longest-priced winner at the meeting since Norton's Coin floored the legendary Desert Orchid in the 1990 Cheltenham Gold Cup.

12. Greece Win Euro 2004 in Portugal’s Back Yard

Greece went into the 2004 European Championships in Portugal as 151.0 outsiders before a remarkable run to glory culminated in a stunning final win over the tournament hosts.

Otto Rehaggel's side edged out Spain to finish runner-up to the Portuguese in the group stage.

The teams finished level on goal difference and couldn't be separated by a tie-breaker either as they had drawn 1-1, so Greece advanced to the knockout phase by virtue of having scored more goals than the Spanish.

They went on to topple France 1-0 in the quarter-finals and then knocked out the Czech Republic in extra-time to set up a final showdown with the hosts. An Angelos Charisteas goal gave Greece a 1-0 fairytale victory and sealed their first ever major tournament triumph.

11. New York Giants win the Super Bowl XLII

Going into the 2007 Super Bowl, the only thing undecided seemed to be the margin of the New England Patriots’ victory. Having won all 16 of their regular season matches, Tom Brady and co. were expected to see off the New York Giants with a minimum of fuss.

As you can probably guess, things did not work out quite like that. The Giants played the game of their lives, with David Tyree’s sensational catch swinging the momentum in his team’s favour. By the end, the Giants were celebrating an unlikely 17-14 victory.

10. Jack Fleck wins the 1955 US Open

John Fleck had only been a full-time golfer for six months before his improbable success at the US Open in 1955. Barely anyone paid attention to him after the first day of action, when the rookie found himself nine strokes down.

Fleck played some excellent golf to fight his way back, but pre-tournament favourite Ben Hogan – who was chasing his fifth US Open title – looked to have one hand on the trophy when he made par on the 72nd hole to reach a total of 287.

But Fleck had other ideas, and it was the 33-year-old who claimed the prize following an 18-hole play-off. He never won another major.

9. The USA beat England at the 1950 World Cup

Going into the 1950 football World Cup, the United States were 501.0 underdogs to win the tournament. They did not quite manage that feat, but they did beat England in what is arguably still the most extraordinary upset in the history of the competition.

To call this David vs Goliath would be to overstate the Americans’ ability. The US had lost their seven matches by an aggregate score of 7-2 and were described as “sheep ready to be slaughtered” ahead of the group-stage game – and that was by their own manager.

But the part-timers triumphed over the professionals thanks to a strike from Joe Gaetjens and some heroic goalkeeping from Frank Borghi, a hearse driver from Missouri.

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8. Japan beat South Africa at the 2015 Rugby World Cup

Japan had only ever won a solitary Rugby World Cup match heading into the 2015 edition of the tournament.

And although they had made progress in the two decades since a 145-17 evisceration by New Zealand, they were still minnows who seemingly had little chance of making any sort of impact in England.

That was until Japan took on South Africa in Pool B’s opening contest. The South Africans were among the leading contenders to win the trophy, and were expected to make light work of Japan in Brighton.

Instead, a thrilling encounter ended in a 34-32 Japanese victory, as the team coached by Eddie Jones upset pre-game odds of 81.0 in what is known as the 'Miracle of Brighton'.

7. United States beat Soviet Union in the ‘Miracle on Ice’

The Soviet Union were the best ice hockey team in the world in 1980. They had already won four gold medals at the Olympics and were heavy favourites to win a fifth in New York, where the United States provided the opposition.

Whereas the Soviet Union team was made up of world-class professionals, the US had to mostly make do with amateur players who turned out for various college teams.

Yet despite that disadvantage, the hosts’ counter-attacking game plan produced a 4-3 victory in the final, sending shockwaves through the sporting world.

6. England beat Australia in the third test of the 1981 Ashes

Between 1989 and 2003, Australia won all eight Ashes Series contested between them and England. Prior to that, it was England who were dominant, beating their old rivals in five of the six editions held between 1977 and 1987.

One of those, 1981, looked to heading Australia’s way. The visitors won the first test by four wickets and then drew the second at Lord’s. The Australians had declared on 401-9 in the third, before England were bowled out for 174, thus resulting in a follow-on.

Odds of 501.0 were offered on an English win, with the hosts floundering on 135-7 in the second innings.

Then up stepped Ian Botham, who scored 149 not out and then handed over to Bob Willis, who took eight wickets as Australia were bowled out for 111. England were victorious by 18 runs and went on to win the series 3-1.

5. James Cahill beats Ronnie O’Sullivan, 2019

Ronnie O’Sullivan has won six Snooker World Championship titles, just one behind Stephen Hendry in the all-time rankings. The Rocket is considered by many to be the greatest snooker player of all time.

That is why it was such a shock when O’Sullivan was dumped out of the 2019 World Championship by an unknown amateur. James Cahill was available at 23.0 to beat the Essex-born maestro in the first round in Sheffield, but he upset the odds to win by 10 frames to eight.

Cahill stormed into an 8-5 lead, but the momentum was with O’Sullivan after the scores were levelled up at 8-8. Remarkably, the 23-year-old won the next two frames to complete the greatest upset in snooker history.

4. Boris Becker wins Wimbledon, 1985

By the time he hung up his racket in 1999, Boris Becker had won six Grand Slam titles – including three at Wimbledon.

His first in 1985 was an astonishing accomplishment, with the 17-year-old becoming the first non-seeded player to win one of the most prestigious competitions in sport.

Pat Cash, Jimmy Connors, John McEnroe, Ivan Lendl, Mats Wilander and Kevin Curren were all more fancied for success than Becker, but it was the German who triumphed.

After he got his hands on the trophy following victory over Curren in the final, one anonymous fan collected a sizeable windfall – he had put A$10,000 on Becker going all the way at odds of 19.0.

3. Emma Raducanu wins the US Open, 2021

Emma Raducanu made a bit of a name for herself at Wimbledon 2021 after a run from the qualifiers to the fourth round on home soil, but a few months later she took the tennis world by storm after winning the US Open against odds of 401.0.

Aged just 18, the scale of her achievement can be quantified by many statistics that emerged in the aftermath of her 6-4 6-3 win over Canadian Leylah Fernandez at Flushing Meadows. She became the first qualifier in the Open era to reach a Grand Slam final, eventually winning it without dropping a set the entire tournament.

She may have gone into the final as a slight favourite over Fernandez, but Raducanu was ranked 150 in the world before the 2021 US Open began, yet the British teenager ended up with the £2million prize money as the dominant winner, blowing away every opponent she came across.

Raducanu also became the first player to win a slam at only the second attempt – the previous record had been in the fourth attempt, set by Monica Seles and Bianca Andreescu. In winning the 2021 US Open, Emma Raducanu arguably produced the biggest upset women’s sport has ever known.

2. Leicester City win the 2015/16 Premier League

Leicester only just avoided relegation to the Championship in 2014/15, winning seven of their final nine matches to complete one of the Premier League’s most impressive great escapes.

Claudio Ranieri replaced Nigel Pearson as manager in the summer and produced an even bigger miracle in 2015/16.

The Foxes were listed as 5001.0 to win the title at the start of the season, with most onlookers tipping them for the drop.

But with the pace and finishing ability of Jamie Vardy, the trickery and guile of Riyad Mahrez, and the ball-winning prowess of N’Golo Kante, Leicester stunned the football world by finishing 10 points clear at the top of the Premier League table.

1. Buster Douglas beats Mike Tyson, 1990

Mike Tyson was the undefeated, undisputed heavyweight champion of the world. Buster Douglas was a 43.0 outsider whose opposition in the ring was supposed to serve as a gentle warm-up for a bout with Evander Holyfield.

Widely considered the best pound-for-pound boxer in the world, Tyson was expected to make light work of his fellow American. Larry Merchant and Jim Lampley, two analysts working for HBO, went as far as to say they thought the fight to be over within 90 seconds.

Instead, it often ranks as the biggest upset in heavyweight boxing history. Douglas made a strong start, immediately letting Tyson know that he was not going to be pushed around easily.

The champion struggled to find his rhythm, and Douglas duly grew in confidence. The knockout blow came in the 10th round and remains one of the most extraordinary moments in boxing history.