5 Biggest Upsets in the History of Sports World
Till now we have seen many teams creating history by winning and by displaying their brilliant performances, but if someone wins, someone has to lose right? Sometimes we don’t get what we expect from any game or life, so let’s dive into the 5 Biggest Upsets in the History of Sports World.
5 Biggest Upsets in the History of Sports World
1) Florida Panthers Beat Boston Bruins – First Round 2023 Stanley Cup Playoffs
The Boston Bruins, entering the 2023 NHL playoffs as the #1 seed, had completed the greatest regular season in NHL history with an astonishing 65-12 record, amassing 135 points.
This historic performance set sky-high expectations for the team, which was stacked with experienced Stanley Cup champions and appeared poised to cap off their record-breaking season with a championship. However, in a stunning turn of events, they faced the #8 seeded Florida Panthers, who had a 42-32 record. Defying the odds, the Panthers pushed the series to a decisive Game 7.
In an outcome that few could have predicted, the Panthers triumphed in Game 7 at TD Garden, eliminating the Bruins and delivering one of the most shocking upsets in NHL playoff history.
This unexpected defeat is widely regarded as one of the biggest chokes in NHL history, as the Bruins’ remarkable regular season ended abruptly and prematurely against a lower-seeded opponent.

2) India Lost the Cricket World Cup Finals 2023
Ah! that pain. Not gonna lie, I mostly don’t watch the entirety of the matches as I am more of a highlights person. But this was one of the rare occasions where I almost watched the entire match live. India was at the top of their game this World Cup season by demolishing any team they faced.
This awakened the dream of many Indians that this might be the year to repeat the 2011 celebration. But it didn’t go that well.
The finals was against Australia who reached the top even when they struggled at the start of the tournament. But by the time they reached the top, they became stronger and stronger.
India batted first and was able to set a total of 240/10, which was not a great score and was tough to defend against Australia.
Australia’s opening pair David Warner and Travis Head we ready to chase but we got some early wickets in the form of David Warner, Mitchell March, and Steve Smith which boosted team India’s morale, but they still had to face the force which eventually broke the bowlers apart.
The partnership between Travis Head and Marnus Labuschagne became the biggest obstacle for Indian bowlers where Travis Head scored a century (137 for 120) and set Australia at a stage of winning before leaving the ground.
Even after getting his wicket the chances of winning were too slim for team India and then Marnus Labuschagne gave the finishing blow which left many of the Indian cricket fans heartbroken.
This was one of the biggest upsets in the history of the sports world.
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3) Buster Douglas Defeats Mike Tyson
In one of boxing’s greatest upsets, Buster Douglas defeated Mike Tyson on February 11, 1990, at the Tokyo Dome.
Tyson, a dominant figure in sports, was heavily favored to win, setting the stage for a future bout with Evander Holyfield and Douglas, entering as a 42-1 underdog, shocked the world with his performance.
Tyson’s corner was unprepared, and his powerful punches did not have their usual impact. In the eighth round, Douglas was knocked down but got up before the count ended. This moment shifted the fight’s momentum significantly.
In the 10th round, Douglas delivered a stunning combination that knocked Tyson down and he failed to beat the referee’s count. This knockout ended Tyson’s reign as the undisputed heavyweight champion.
The upset became an iconic moment in sports history. Douglas’ victory proved that determination could overcome the odds. Tyson’s aura of invincibility was shattered. The fight exposed vulnerabilities in Tyson’s training and preparation.
Douglas dedicated the win to his mother, who had passed away shortly before the fight. The victory catapulted Douglas into the limelight, making him a global sensation overnight.
This fight is known as one of the greatest upsets in sports history. Tyson’s loss was a significant turning point in his career. The fight demonstrated that no athlete is unbeatable.

4) 1960 World Series – Pirates defeat Yankees
Date: October 13, 1960
Final Score: Pirates win Series 4-3
In the late 1950s and early 1960s, the New York Yankees were an unstoppable dynasty with stars like Mickey Mantle, Yogi Berra, Whitey Ford, and Roger Maris. The 1960 Yankees won their 11th American League title in 14 years. In contrast, the Pittsburgh Pirates had just won their first pennant since 1927.
The 1960 World Series was a rollercoaster. The Pirates won Game 1 (6-4) but were demolished in Games 2 (16-3) and 3 (10-0). Surprisingly, they bounced back to win Games 4 and 5 at Yankee Stadium. After losing Game 6 in Pittsburgh (12-0), the series was tied, setting the stage for a dramatic Game 7.
Game 7 ended with one of the most famous home runs in baseball history. Bill Mazeroski hit a walk-off homer off Yankees reliever Ralph Terry, winning the game 10-9 and the series for the Pirates. Despite being outscored 55-27 in the series, the Pirates’ victory remains one of the most iconic feat in the history of the sport.
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5) Leicester City 2015-16 Premier League Champions
Date: May 2, 2016
Final Record: 23-12-3 (81 points)
Leicester City’s triumph in the 2015-16 Premier League season is one of the greatest underdog stories in sports history. Entering the season, many predicted Leicester would be relegated, with the team facing 5000:1 odds of winning the league.
Defying all expectations, Leicester, led by Jamie Vardy’s record-breaking goal-scoring streak, clinched the title that year.
Key players like Riyad Mahrez and N’Golo Kanté delivered outstanding performances, contributing significantly to the team’s success. Manager Claudio Ranieri, initially doubted by many, orchestrated a masterful campaign, emphasizing teamwork and resilience. Leicester’s defensive solidity, anchored by captain Wes Morgan and goalkeeper Kasper Schmeichel, was crucial throughout the season.
Leicester City mathematically secured the championship on May 2, 2016, when Chelsea drew at home against Tottenham Hotspur. This draw left Leicester seven points clear at the top, an insurmountable lead with two games remaining. The victory sparked celebrations across Leicester and the football world, with fans and neutrals alike marveling at the team’s achievement.
This achievement is celebrated as one of the most extraordinary successes in sports betting history, showcasing Leicester City’s resilience and determination. Their victory inspired countless fans and remains a testament to the unpredictable and thrilling nature of sports. Leicester City’s 2015-16 season will forever be remembered as a triumph of the underdog, demonstrating that with hard work and belief, even the most unlikely dreams can come true.
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5 Biggest Upsets in the History of Sports World
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