Upsets are one of the reasons we love sport.

The excitement of watching a sporting giant crumble before your eyes and the thrill of being able to say “I was there” as a new name announces itself to the world.

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Biggest Sports Upsets:

But it’s not just the spectacle that makes shock results so exciting. History’s biggest sports upsets are loved by gamblers the world over for the enormous payouts they can provide.

Put a tenner on a 500-1 outsider to win the Premier League at the start of the season, and you could be claiming a small fortune come May.

Biggest Upsets In Boxing History

Lennox Lewis was a household name going into his fight with American challenger Hasim Rahman, known the world over as one of the boxers of his generation.

But Rahman was not the first choice opponent for the man who had lost only once in 39 bouts.

Instead, he was Lewis’s back-up option after a fight with his more favoured opponent Mike Tyson fell through after the legendary American fighter was given a three-month suspension for a failed drugs test following his fight against Andrew Golota.

As such, Lewis went into this fight shrouded in hubris. Rahman, however, was far more focused on the job at hand and it showed.


The first four rounds of this now legendary fight were tightly contested, with Lewis just edging Rahman on points. But the arrogance that had characterised Lewis’s preparation for the fight finally caught up with him in the fifth round.

Backed up against the ropes, he allowed his hands to fall from his face, giving Rahman the opportunity to land his infamous right hand jab square on Lewis’s jaw, leaving the world champion in a heap on the canvas.

Unable to get back up, the man who had successfully defended his world champion title three times, was forced to surrender the status of Heavyweight Champion of the World to the 20-1 outsider.

A rematch was held seven months later in November 2001 in which Lewis would eventually win back his belts, but Rahman’s initial victory will surely go down as one of the best boxing fights ever.

Biggest Upsets In Football History

Euro 2004 was notable for a number of different reasons. Wayne Rooney’s explosion onto the European stage, a French side packed with exquisite footballing talent and a bright young thing in the Portugal side called Cristiano Ronaldo.

But the real story of that tournament was claimed by the eventual winners, Greece.

Rank outsiders from the start, Greece were 150-1 to win the tournament outright, but thanks to a fiercely determined style of play, they became part of the one of the greatest football underdog stories ever. 

They started the tournament off on the right foot, beating hosts Portugal 2-1. And despite a draw and a loss in their final two group games, they proceeded to the knockout stage on goal-difference and never looked back.

1-0 wins against defending Champions France in the quarter-finals and the hotly-tipped Czech Republic in the semis set up a meeting in the final with Portugal, a repeat of the opening game of the tournament.


Despite endless pressure from a star studded Portugal team that featured the likes of Ronaldo, Luis Figo and Rui Costa, the Greeks held out, patiently waiting for their opening.

And they found it, as Angelos Charisteas rose highest to meet a corner, nodding home past a sprawling Ricardo in goal.

Charisteas’s strike was enough to earn the Greeks a truly astounding victory in a tournament they went into holding only modest hopes of potential knockout round qualification. 

They would go out of the group stages with three consecutive losses at the next European Championships four years later, but their astonishing underdog success in Portugal stands the test of time to this day as one of the greatest sports upsets of the last 20 years.

Biggest Upsets In NBA History

Having cemented his status as a legend of the game with consecutive NBA titles for Miami Heat in 2012 and 2013, LeBron James returned to his hometown team of the Cleveland Cavaliers in 2016 with the aim of bringing that same success to a city deprived of any sporting glory for over half a century. 

The Cav’s route to the title, however, was nothing short of sensational in what would be one of the greatest underdog sports stories ever.

Having won the Eastern Conference, the Cleveland Cavaliers were pitted against Western Conference and defending NBA champions, the Golden State Warriors.


But the Warriors had set the record number of wins in the regular season, claiming a sensational 73 wins to 9, and before long, the Cavs found themselves 3-1 down in the series.

But thanks to inspirational performances from James, Kyrie Irving and Tristan Thompson, the Cavs were able to level the series and earn a decisive seventh game.

In typically dominant fashion, James took the game to Warriors scoring 27 points as his side edged a famous victory that saw them become the first team to win a series from 3-1 down.

The Game 7 victory in California was also the first time since 1978 that a seventh match had been won by the away side, marking LeBon James’ Cavs out as arguably the greatest NBA underdog champions ever.

Biggest Upsets In NFL History

While the NFL has thrown up some of the greatest Cinderella stories in sports history, few come close to the New York Giants’ victory in Super Bowl XLII.

After a less than perfect run in the regular season, in which they won only 10 of their 16 games, they found themselves in the Super Bowl with the opportunity to become the first Wildcard team from the NFC to claim the title.

Their opponents, however, couldn’t have been more difficult to overcome. The New England Patriots had just finished the regular season undefeated and went into the showdown with their cross-state rivals as 12 point favourites. 

But in a game that was defined more by the defensive solidity of both sides, it took a moment of magic for the Giants to make the breakthrough.


Down 4 points in the fourth quarter with 2 minutes 39 left on the clock, the Giants regained possession on their own 17-yard line and proceeded to drive the remaining 83-yards up the field.

This handed wide receiver Palexico Burress the opportunity to score the winning touchdown with 35 seconds remaining in what was one of the last plays of the game.

That play could not have happened, however, were it not for David Tyree’s infamous “helmet catch”, in which he caught a 32-yard pass one handed in mid-air, holding the football against the top of his helmet in order to keep it away from the challenging Rodney Harrison. 

The Giants held on for the win, earning them only their third ever Super Bowl in a victory that dwarfs any regular season NFL upsets of the week.

Biggest Upsets In Sports History Odds

Laying your bets on a potential upset may not be the best strategy long term, but when it pays off, it pays off spectacularly.

At no point was this more evident than in the 2015/16 Premier League season when lowly Leicester City dared to challenge English football’s elite for the title against odds of 5000-1. 

In a season where England’s usually dominant forces were plagued with inconsistency and the burden of managing still developing squads, Leicester rose above the rest by playing a style of break football that was fast, direct, and at times, glorious to watch.

Spearheaded by a strike force of Jamie Vardy, Riyad Mahrez and Shinzi Okazaki and backed up by the defensive nous of Wes Morgan, Robert Huth and N’Golo Kante, the Foxes tore apart teams they wouldn't have had a hope of beating the year before.


Having barely survived by the skin of their teeth the previous season, Leicester’s title odds were priced against odds of 5000-1 before the start of the season.

But come May and there were hundreds of stories of punters who had just won big on one of the underdog sports betting moments of the century. 

With odds so long, just a small stake would’ve raked in a truly life changing amount of money, with one punter claiming £20,000 in winnings from just a £4 bet.

Even those who couldn’t bear to hold out till the end of the season and chose to cash out instead claimed big money, including one man who decided to take home £29,000 from a bet that could have seen him win £100,000 if he’d just waited a few weeks longer.


*Credit for the main photo belongs to Frank Augstein / AP Photo*

 

FIRST PUBLISHED: 17th November 2020

The 888sport blog, based at 888 Towers in the heart of London, employs an army of betting and tipping experts for your daily punting pleasure, as well as an irreverent, and occasionally opinionated, look at the absolute madness that is the world of sport.