Top 5 greatest upsets in modern football history
From Leicester City's miraculous 2015/16 Premier League, to Grimsby Town's stunning Carabao Cup win over Manchester United in 2025, here are the top five greatest upsets in modern football history.
Last Updated: 07.59 PM, Aug 28, 2025
Football, the beautiful game, is one of the most-watched and loved sports in the world because it gives every team the opportunity to chase their dreams and go toe-to-toe against some of the biggest teams in history. This allows the fans to see a few of the greatest upsets in football history every now and then. With fourth-division club Grimsby Town beating Premier League club Manchester United in the Carabao Cup second round, we present you with some of the greatest upsets in modern football history.
1. Leicester City winning the Premier League in 2015/16
Now this is not just any game; it is about winning the whole tournament. Out of the movie scripts, Leicester City achieved something which no one thought they could achieve.
In the 2015/16 season, under manager Claudio Ranieri, they went on to lift the Premier League title after finishing 14th the previous season.
With 81 points, they finished 10 points ahead of Arsenal to win the league. Jamie Vardie, who scored in 11 straight games, finished the season with 24 goals and won the Premier League Player of the Season Award as well.
Read Also: Crystal Palace clinch historic 2025 Community Shield after penalty heroics from Henderson
2. Grimsby Town 2-2 Manchester United in the 2025 Carabao Cup
In one of the most stunning recent upsets, fourth-tier club Grimsby Town shocked Premier League giants Manchester United by drawing 2-2 and then winning 12-11 on penalties in the Carabao Cup second round at Blundell Park.
Grimsby raced to a 2-0 halftime lead, with Charles Vernam and former United youth player Tyrell Warren scoring.
Despite a late United comeback led by Bryan Mbeumo and Harry Maguire, the League 2 side held their nerve in an epic shootout lasting 26 penalties.
Manchester United is valued at €887.20m while Grimsby Town is valued at €3.60m. You can now think about why this is called one of the greatest upsets in modern football history.
3. Greece 1-0 Portugal in Euro 2004 final
Greece clinched one of the biggest international shocks by defeating heavily favoured host nation Portugal 1-0 in the Euro 2004 final.
Portugal, with stars like Cristiano Ronaldo, were expected to dominate, but Angelos Charisteas’s header in the 57th minute and a resilient defensive effort stunned the home crowd.
Greece’s unexpected victory is considered one of European football's greatest moments of tactical discipline.
4. Saudi Arabia 2-1 Argentina in 2022 World Cup
Where is Messi? This famous, or you can say infamous, troll from anti-Lionel Messi fans came to life when Saudi Arabia shockingly defeated Argentina in the group stage of the FIFA World Cup 2022 in Qatar.
Lionel Messi’s early penalty could not secure victory for Argentina, as Saleh Al-Shehri and Salem Al-Dawsari scored second-half goals for Saudi Arabia.
Post this match, Messi had asked the fans to keep faith in the team, and they were treated with one of the greatest FIFA World Cup moments when Messi and company lifted the 2022 World Cup despite the early setback against Saudi Arabia.
5. Wimbledon 1-0 Liverpool in 1988 FA Cup Final
Wimbledon's FA Cup win over Liverpool in 1988 is a classic underdog story.
Although Wimbledon was only seventh in the top flight, Liverpool were the dominant force in English football and favorites to add the FA Cup to their league title.
A stunning header from Lawrie Sanchez gave Wimbledon an early lead, which they held onto with rugged defence to triumph at Wembley.
The victory earned Wimbledon the nickname "The Crazy Gang," beating the "Culture Club," and remains one of the most memorable and shocking results in English football history.