30 Sports Legends Who Suffered Stunning Defeats

Darren - June 15, 2021

30 Sports Legends Who Suffered Stunning Defeats

Darren - June 15, 2021

18. Conor McGregor (2021)

McGregor rocked up to Abu Dhabi in 2021 on a yacht. The Irishman hadn’t fought for a year after beating Donald Cerrone in style. His next fight was a rematch against Dustin Poirer. He was supremely confident because he had already knocked The Diamond out in their previous meeting. But lighting doesn’t strike twice in the same place. McGregor discovered this the hard way.

In short, “The Notorious” and his team made a massive mistake. They looked past Poirier and towards a potentially lucrative boxing match against Manny Pacquaio. However, they paid a massive price because Poirier unleashed the perfect game plan. He targeted McGregor’s calves and compromised the Irish fighter badly. Then, he finished McGregor off with a brutal knockout and McGregor received what he deserved.

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17. Kurt Warner

It wasn’t supposed to be this way. The Rams were back in the Super Bowl for the second time in three seasons. Meanwhile, their 14-2 record was an NFL best, and their quarterback Warner was outstanding. It seemed impossible that they would lose the showpiece event. Their opponents in New Orleans were the Patriots. After establishing a solid 11-5 record, not many people fancied them to win. They also had a first-season starter by the name of Tom Brady.

The sixth-rounder had a brilliant game and won Super Bowl MVP honors. In short, the Patriots stopped ‘The Greatest Show on Earth’ and won the game. It came down to the wire as the Patriots scored from the final play. Adam Vinatieri kicked the game-winning field goal as time expired. This was a great victory for New England but one of the most painful defeats of Warner’s career.

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16. Ben Askren (2021)

YouTuber Jake Paul challenged Askren to a boxing match and immediately split the combat sports world. As a former Bellator and ONE champion, Askren had a formidable pedigree. He was also an Olympic wrestler. However, his striking left a lot to be desired as MMA fans saw when he fought for the UFC. But surely, he could beat a YouTuber? Most of his MMA compatriots stayed loyal to Askren and supported him.

Unfortunately, Askren suffered one of the most embarrassing defeats of his career. This was arguably worse than his five-second KO loss to Jorge Masvidal. At least ‘Gamebred’ was a real opponent. To sum up, Paul knocked Askren out in the first round. There really isn’t much more to say except Askren received a big paycheck, so at least his bank balance was happy, but his fans definitely didn’t enjoy this.

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15. Muhammad Ali (1978)

Ali suffered numerous defeats throughout his career. However, only one man was able to take his titles away inside the ring. That boxer was Leon Spinks. Spinks came into this fight as an Olympic gold medalist. But he only had six professional fights to his name. Needless to say, Ali was a massive favorite when they met in Las Vegas. But the bookmakers endured a hard day at the office.

This was the upset of the year. Spinks unsettled Ali and stayed game throughout the entire fight. Finally, the bout went to a decision. Two of the judges scored it in favor of Spinks while one gave it to the champion. Later, Ali reclaimed his titles in a rematch. He defeated Spinks by unanimous decision on that night. This was a tremendous result for his young opponent.

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14. Greg Norman (1996)

Norman is an Australian golfing legend. Who doesn’t love the Great White Shark? Perhaps he didn’t love himself in 1996 after an embarrassing display on the final day of the Masters. The craziest aspect of this was that he shot an opening-round 63 on the first day. This was a course record, but he couldn’t sustain it. Finally, he played with Nick Faldo and ran out of gas.

Somehow, he contrived to lose by a large margin. Norman had three straight bogies on the ninth through to the 11th holes. Then, he had a double-bogey on the 12th. It was a car crash of a performance and he basically handed Faldo the win. Faldo came into this game with no real expectations because he was so far behind. But somehow, Norman endured one of the most bizarre defeats in golf.

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13. Steven Gerrard (2014)

Gerrard played spent 17 seasons with Liverpool’s senior team after emerging from the youth ranks. The dynamic midfielder became a central figure for club and country. After captaining the team to Champion’s League and F.A Cup glory, he became an icon. However, Gerrard also endured several painful moments throughout his years with his beloved Reds. The worst came against Chelsea in 2014.

Liverpool came very close to an elusive Premier League title win. They knew that victory over Chelsea would likely see them secure the coveted prize. Tragically, Gerrard slipped up at the worst moment. He lost his footing and allowed Chelsea striker Demba Ba to score. It was a nightmare for the loyal captain. Gerrard lost games by bigger margins but he was personally responsible for the cruelest of defeats.

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12. Tim Duncan (2004)

International basketball is typically uncompetitive when the US sends its strongest team. The talent pool is ridiculous because all the players are NBA stars. This makes it very difficult for other countries to compete against them. While there are other strong basketball nations, it’s unusual for the US to suffer defeats. However, they do occur, and it’s always big news when they happen.

In 2004, the USA met Puerto Rico in the Olympic Games. But Puerto Rico won the game against all of the odds. This was very humiliating for States because they lost to their own territory. Meanwhile, the likes of Duncan and Allen Iverson played for the USA so they had strong talent. Of course, Puerto Rico had NBA stars in their ranks too. But this was an island of four million against a nation of 330 million.

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11. Mirko Cro Cop (2015)

Few fighters carry a mystique like Mirko Cro Cop. The Croatian legend won kickboxing titles before he transitioned to MMA. He built up his reputation in Japan under the PRIDE banner before he moved to the USA. There was a lot of hype around his name when the UFC finally signed him. He won his debut but then he ran into Gabriel Gonzaga, where Cro Cop was an overwhelming favorite.

The Croatian’s left kick was the stuff of legend. “Right kick hospital, left kick cemetery” was his classic catchphrase. His fight against Gonzaga was a title eliminator. Most people believed that it was a foregone conclusion but Gonzaga pulled off the upset. Furthermore, he did so in the most shocking manner. Gonzaga unleashed a left-high kick of his own to KO Cro Cop in style.

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10. David Luiz (2014)

Luiz captained Brazil on this fateful day in World Cup history. They met Brazil in the semifinals of the 2014 tournament, in Belo Horizonte. The two teams came into this game undefeated and fans expected a close game. However, instead, they bore witness to one of the most humiliating defeats in Brazilian soccer history. Germany ran out 7-1 winners on a traumatic night for the Samba nation.

Brazil was without their star player Neymar and their most important defender Thiago Silva. But nobody expected them to capitulate in the manner that they did. Germany scored four goals in the space of seven minutes in the first half as they ran riot. The Germans were bemused because it was so easy for them. Luiz was hapless as his team fell to bits around him. It was a nightmarish experience for the Brazilians.

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9. Bob Stoops (2007)

The Oklahoma Sooners are one of college football’s most iconic programs. Stoops coached the Sooners for almost 20 years. He was a two-time Walter Camp College Coach of the Year and also won multiple Big 12 Awards. Meanwhile, in 2021, he received confirmation of his induction into the College Football Hall of Fame. However, even the best coaches suffer upsets and defeats.

In 2007, the Sooners played the WAC’s Boise State in the Fiesta Bowl. Oklahoma built up a massive lead but the Broncos refused to give up. Toward the end of the game, they pulled off three crazy trick plays to win. It was an insane back-and-forth game of football. Almost everybody fancied the Sooners before this one. However, Boise State did themselves proud and emerged victoriously.

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8. Jose Aldo (2015)

Aldo established himself as the best featherweight fighter on the planet, becoming a WEC and then-UFC champion for eight years. Nobody was able to put him in serious trouble. The likes of Chad Mendes and Frankie Edgar challenged him but were unable to take his crown. But along came an Irish upstart by the name of Conor McGregor. His rise was unprecedented and he swiftly obtained a title shot.

The build-up to this fight was grueling. The two men went on a world tour to promote the fight and Aldo suffered mental fatigue as a result. However, McGregor reveled in it and used it as a weapon against his opponent. When the fight finally arrived, Aldo waded forward with guns blazing. The Notorious caught him with a counter left and knocked him unconscious in 14 seconds. It was an iconic moment.

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7. Patrick Ewing (1985)

Georgetown was all-conquering in 1984. A year later, they were back. Ewing was the team’s superstar and all basketball fans knew that he was a special player. Later, his NBA career reflected this. He is one of the New York Knicks’ greatest-ever athletes. However, in ’85, Ewing suffered one of the first major setbacks of his basketball life. To be fair, it set him up well for his long Knicks tenure.

The school had the chance to win back-to-back championships. Only lowly Villanova stood in their way. Villanova lost ten games throughout the season. Because of this, nobody gave them much of a chance. Unfortunately, for Ewing and Georgetown, their opponents were up for this game. This was one of the most stunning victories in college basketball history.

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6. Cristiano Ronaldo (2004)

Greece was never a soccer powerhouse. However, the Mediterranean nation achieved one of the most stunning results in the sport’s history. Euro 2004 went down in Portugal. The host nation lost to Greece in the opening game but progressed to the final anyway. They had an incredibly rare opportunity to win the trophy in their own country. Meanwhile, they had a chance to get revenge against the unfancied Greeks.

The Greeks were massive outsiders before the tournament but obviously, nobody told them this. Portugal had the likes of Figo, Deco, and Ronaldo in their team. But this star power wasn’t enough to defeat the Greeks. Nobody knew half of the players in the Greek squad but they held firm, In the end, they ground out a 1-0 victory. Furthermore, they inflicted the most painful of defeats on Ronaldo and his team.

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5. Ronnie O’Sullivan (2019)

Most people accept O’Sullivan is the greatest snooker player of all time. The UK star is a six-time world champion. Meanwhile, he also has seven Masters titles to his name. Infamously volatile, O’Sullivan is always box office material. However, even the best suffer defeats and O’Sullivan is no exception. He lost in shocking circumstances against an unknown amateur.

The likes of golf and snooker are fascinating because brilliant individuals occasionally materialize. In this case, James Cahill came out of the woodwork and inflicted a crushing defeat on O’Sullivan. Nobody expected him to stand a chance against the world number one. Meanwhile, Cahill also defeated another world champion in Mark Selby. Sometimes it’s impossible to predict what will happen.

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4. Conor McGregor (2016)

McGregor was on course to become the UFC’s first simultaneous two-weight world champion. After he won the featherweight title, he moved up a division to face Rafael dos Anjos. However, McGregor agreed to face Nate Diaz on short notice when lightweight champ dos Anjos suffered a foot injury. He didn’t want his traveling Irish fans to come all the way to Las Vegas for nothing. But things didn’t go the way he expected.

The fight was at welterweight because Diaz didn’t have time to make the 155 lb. limit. McGregor pieced Diaz up for one-and-a-half rounds. But then he ran out of gas and Diaz clipped him. The Irishman shot for a takedown in desperation but Diaz ended up choking him out. Before this, McGregor seemed invincible. This was one of the most shocking defeats in UFC history because of the circumstances and drama.

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3. Mike Tyson (1990)

Tyson was the most feared fighter on the planet in 1990. The heavyweight champion of the world held three titles and built up a record of 37-0. All of his opponents knew that they were likely to leave the ring unconscious. But then along came Buster Douglas to upset the apple cart. Tyson agreed to fight Douglas in Tokyodome, Japan. It was essentially a tuneup fight for a proposed bout against Evander Holyfield.

Nobody gave Douglas a chance. Tyson’s corner team didn’t even bring ice because they were so convinced of their fighter’s superiority. However, Douglas produced a stunning upset. He used his jab efficiently and effectively to shut Tyson’s eye. Then he went to work and got the finish in the tenth round. Later, it emerged that Tyson partied all night in Tokyo. But it was still one of the most shocking defeats in the history of boxing.

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2. Ronda Rousey (2015)

Rousey was unstoppable until she ran into Holly Holm. The bantamweight champion’s exploits convinced UFC President Dana White to open up women’s divisions. She went on a tear and crushed her opponents with her judo skills. Furthermore, she became a genuine superstar in the process. But it all came to an end one night in Melbourne, Australia, when ‘The Preacher’s Daughter’ took her title away.

Holm executed the perfect game plan against Rousey. She used footwork to evade Rousey’s takedown attempts and outboxed her on the feet. But Rousey continued to strike with Holm. This proved fatal because Holm lit her up and finally knocked her out in the second round. Everybody expected Rousey to add Holm to her list of scalps. In the end, she lost her crown in brutal circumstances.

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1. Dan Marino (1999)

Marino led the Miami Dolphins for the entirety of his NFL career. One of the best quarterbacks of his generation, he unfortunately never won a Super Bowl. This is a bit of a travesty because he was definitely worthy of a ring. However, the players around him weren’t always of a high enough standard to make Miami competitive. His final appearance came in 1999 when he suffered one of the worst defeats of his career.

Miami played the Jacksonville Jaguars in a playoff game. Everybody knew that this was Marino’s final season. But they thought that his team might contend for a final time. In the end, that’s not what happened. The Dolphins were more like goldfish as the hungry Jaguars destroyed them. Jacksonville won 62-7 after totally destroying their opponents. It was a shame for Marino as he played terribly as well.

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30 Sports Legends Who Suffered Stunning Defeats