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Reading: The Biggest Upsets in Modern Football History
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Football

The Biggest Upsets in Modern Football History

watchdog
Last updated: 5th September 2025 at 15:46 3:46 pm
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Football is a game of passion, tactics, and sometimes — pure madness. Over the decades, the sport has given us stories that are too unbelievable to forget. While giants usually dominate the stage, every now and then, a David rises to stun a Goliath. These are the moments that remind us why we watch football: not just for the skills or the goals, but for the unexpected twists that make history. Let’s take a walk through some of the biggest upsets in modern football history that left fans speechless, pundits baffled, and underdogs forever remembered. These were moments you could have wagered on with Chicken Road Casino.

Contents
Leicester City Winning the Premier League (2015/16)Greece Wins Euro 2004Barcelona 2-8 Bayern Munich (2020 UEFA Champions League)Chelsea vs. Bayern Munich – 2012 Champions League FinalJapan Beats Germany – 2022 World CupHow Upsets Influence Club and National Team RebuildingConclusion

Leicester City Winning the Premier League (2015/16)

So we will begin with what is one of the more amazing modern football fairytales: the 2015/16 Premier League win by Leicester City. The bookmakers pegged them at 5,000-1 pre-season in winning the title. It is a club which only last season had very closely avoided being relegated. They possessed a new controversial coach, Claudio Ranieri, and a team with all kinds of hidden talent: Jamie Vardy, Riyad Mahrez, N;Golo Kant, and Wes Morgan.

But week after week, they proved to be the surprise package by outclassing the best of the clubs such as Manchester City, Liverpool and Chelsea by fighting till the final whistle. Records were broken by Vardy. Mahrez jived past opponents. Kant (e) trod each blade of grass. By May they were English champions, and the world stood astonished. The victory of Leicester was not only a sports miracle but a lesson that the world should not forget that football is a game where even in the most magic world things come true.

Greece Wins Euro 2004

When the UEFA Euro 2004 started in Portugal, nobody liked Greece and there was no Chicken Road gambling. They had previously never won a major tournament and were not supposed to go through the group stages. Coach Otto Rehhagel however had different plans. Greece defended through a disciplined style that left some of the best teams in the world frustrated.

They defeated hosts Portugal in their first game and eliminated defending champions France in the quarterfinals and narrowly defeated a talented Czech Republic team in the semifinals. The final? A second battle with Portugal–on this occasion at Lisbon. Greece became the winner with a score of 1 to 0, courtesy of a header by Angelos Charisteas. Only safe betting strategies for football matches could have saved one from loss in this game.

Barcelona 2-8 Bayern Munich (2020 UEFA Champions League)

Not many people describe the defeat of a dominant team as the upset, but the 8-2 loss of Barcelona against Bayern Munich in the quarter final stage of the 2020 Champions League competition was exactly that. It was not a loss, it was a breaking up, considered one of the most unforgettable football matches.

Messi, Suarez and Griezmann were in Barcelona. Bayern were a good team, yet nobody feared that they will slaughter such a club with the pedigree of Barcelona. The game was a nightmare to the fans of Barcelona as Bayern was playing with all lightning moves and furthermore the team was able to shoot at will.

Chelsea vs. Bayern Munich – 2012 Champions League Final

Chelsea had reached the final in 2012 in one of their worst domestic seasons in recent memory. They were heavy underdogs against Bayern Munich, who were playing at their home ground, the Allianz Arena.

Bayern dominated the match but couldn’t finish it off. Then, in the 88th minute, Didier Drogba headed in an equalizer. Chelsea held on, took the game to penalties, and won. Drogba, in what was to be his last kick for the club at the time, scored the winning penalty. Chelsea’s win was unexpected, emotional, and a perfect underdog finish to a chaotic season.

Japan Beats Germany – 2022 World Cup

In the Group phases of the 2022 FIFA world cup in Qatar, Japan staged a remarkable comeback to edge four-time winners Germany 2-1. It was not a consequence, it was a process. In the second half Japan was faster and calmer which beat the Germans.

The loss surprised even the fans across the globe, and Germany plunged into disarray that ultimately saw them fail to get out of the group stage or the second World Cup in a row. To Japan, it was an indication of how international football had turned out to be where training, organization, and tactics were more dominant than heritage and star players. It was one of the best sports news for gambling fans in Japan.

How Upsets Influence Club and National Team Rebuilding

Some defeats are so shocking they trigger massive changes:

  • Barcelona’s 8-2 loss led to new management, presidential elections, and Messi’s exit.
  • Germany’s 2018 and 2022 World Cup exits led to soul-searching in the DFB and major team reshuffles.
  • Brazil’s 7-1 loss initiated a more pragmatic approach to team building.

Conclusion

Football is beautiful not only when it is perfect but it is also beautiful when it is unpredictable. Such upsets are a reminder that the game is not scored on paper. It is the team spirit, the courage and the faith which can tame the rich clubs, the big names and the glowing reputations. Upsets most certainly are the lifeblood of the football world, be it a small country who managed to secure a continental cup event or a relegation strapped side that has managed to bring home the biggest league crown.

They turn us to dreamers. They remind us that at the opportune second, anybody, however petite, can turn the page. That is why football will never be only a game.

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