The most painful penalty misses in football history

Penalty shootouts are football’s ultimate test of nerve, often turning players into heroes or villains in the space of seconds. Over the years, many of the sport’s most dramatic moments have been defined by missed penalties. These heartbreaking moments can stay etched in the memories of fans and players for generations.

From World Cup heartbreak to Champions League anguish, missed penalties have shaped footballing history. Here, we'll revisit some of the most painful and unforgettable penalty misses in football.

Antoine Griezmann’s missed penalty in the 46th minute during the 2016 Champions League final against bitter rivals Real Madrid proved costly. His shot struck the crossbar, and Atlético Madrid went on to lose 5-3 in a dramatic shootout after the game ended 1-1, securing a record-extending 11th title in the competition for Los Blancos. Atleti, meanwhile, still have zero titles to their name.

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In their quarter-final against France, England captain Harry Kane had the chance to equalise late in the battle of the 2022 World Cup's two favourites. However, he blasted his second penalty of the night high over the bar, ending the Three Lions’ hopes of glory in Qatar. France, meanwhile, would get beaten in the final by Argentina.

Italy hosted the 1990 World Cup and were favourites to win as they faced Argentina in the semi-final in Naples. The match ended 1–1 after extra time, leading to a tense penalty shootout. Roberto Donadoni’s attempt was saved by Sergio Goycochea, turning the tide in Argentina’s favour. The miss was a crushing blow for Italy, who had hoped to lift the trophy on home soil.

France’s Kylian Mbappé missed the decisive penalty in a shootout against Switzerland in the Euro 2020 round of 16. His shot, saved high by Swiss goalkeeper Yann Sommer, saw France, the reigning World Cup champions and the pre-tournament favourites, eliminated in a major upset.

In the 1986 World Cup quarter-final, Brazil faced France in Guadalajara, Mexico, in what would become one of the most dramatic matches in tournament history. One major flashpoint was when Brazilian legend Zico saw his penalty during normal time saved by Joel Bats. The miss, a rare blemish on the career of one of football’s greats, proved costly as the game finished 1-1 and Brazil went on to lose 4-3 in the shootout (even though Zico himself scored his penalty).

England were just one step away from the Euro 1996 final when they faced Germany at Wembley. After a tense 1–1 draw, the game went to a penalty shootout. The future national team manager stepped up for the Three Lions’ sixth penalty, but his low effort was saved by Andreas Köpke. Germany converted their next penalty, eliminating England and breaking the hearts of a nation hoping for glory on home soil.

In the 2016 Copa América final, Lionel Messi missed Argentina’s first penalty in the shootout against Chile. The miss set the tone for Argentina’s defeat, marking Messi’s third consecutive final loss in three years. Overcome with emotion, Messi announced his international retirement shortly after, only to return later—with a vengeance.

Following Wayne Rooney's injury, England’s Darius Vassell was thrust into the spotlight early on during the Euro 2004 quarter-final shootout against Portugal. His penalty, England's sixth, was saved by Ricardo, who dramatically removed his gloves before making the stop. Vassell’s miss confirmed yet another premature tournament exit for England’s so-called Golden Generation, and Ricardo’s theatrics became one of the enduring images of the tournament, eventually won by Greece.

With the scores tied 1–1 in the dying minutes of normal time during the 1999 FA Cup semi-final replay, Arsenal’s Dennis Bergkamp had a golden opportunity to secure victory against Manchester United. Awarded a penalty after a clumsy foul by Phil Neville, Bergkamp stepped up but saw his low shot brilliantly saved by Peter Schmeichel. The game went into extra time, where Ryan Giggs scored his legendary solo goal to send United to the final. Bergkamp’s miss not only ended Arsenal’s hopes of retaining the trophy but also proved to be one of the pivotal moments of United’s Treble-winning season.

With the opportunity to seal his team’s first-ever Champions League title, Chelsea captain John Terry stepped up to take his side's fifth spot-kick in the 2008 final shootout against Manchester United. However, as he struck the ball, he slipped on the wet Moscow turf, and his shot hit the post. The shootout went to sudden death and United eventually triumphed, leaving Terry heartbroken.

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Ghana stood on the brink of history in the 2010 World Cup quarter-final against Uruguay. With the scores level in the final seconds of extra time, Asamoah Gyan was awarded a penalty after Luis Suárez’s deliberate handball. Gyan’s effort smashed against the crossbar, and Ghana ultimately lost the game on a penalty shootout. It was a heartbreaking end to a tournament where Ghana had captured the hearts of fans around the globe.

With Leicester City needing a goal to secure their place in the Championship play-off final, Anthony Knockaert stepped up for a stoppage-time penalty against Watford. His weak shot was saved by goalkeeper Manuel Almunia, who also blocked the rebound. Watford launched an immediate counter-attack, scoring through Troy Deeney in one of football’s most dramatic moments. The turn of events sent Leicester crashing out and Watford into the final.

The Euro 2020 final marked England's first appearance in a major tournament final since 1966. With the chance to level the scores in the shootout after Jordan Pickford denied Jorginho, 19-year-old Bukayo Saka stepped up to take the decisive fifth penalty. Gianluigi Donnarumma dived to his left to save, sparking scenes of jubilation for Italy and despair for England—again.

In one of the Premier League’s most heated encounters, Manchester United faced Arsenal at Old Trafford in September 2003. A late penalty awarded to United gave Ruud van Nistelrooy the chance to clinch victory, but his powerful shot struck the crossbar. Arsenal players, especially Martin Keown, infamously taunted him after the miss, and the match ended in a goalless draw. This moment proved pivotal for Arsenal, as they went on to finish the season unbeaten.

England’s semi-final against West Germany in the 1990 World Cup was a tense affair, ending 1–1 after extra time. In the shootout, Stuart Pearce’s penalty was low and hard, but goalkeeper Bodo Illgner guessed correctly and saved it with ease. The miss visibly crushed Pearce, who broke down in tears as England were eliminated. Following Pearce’s miss, Chris Waddle had to score. Instead, his shot sailed high over the bar, ending England’s dream of reaching the final and immortalising one of the most painful moments in England’s footballing history. It would take six years for Pearce to redeem himself with a successful penalty at Euro 1996.

The Netherlands were favourites to progress in their Euro 2000 semi-final against Italy, played in Amsterdam in front of a raucous home crowd. But during the penalty shootout, defender Jaap Stam took a thunderous shot that soared over the bar. His miss shifted momentum to the Italians, who went on to lose the final to France.

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Italy's hopes rested on the shoulders of Roberto Baggio, one of the greatest players of his generation, in the 1994 World Cup final against Brazil. With Italy trailing 3–2 in the penalty shootout, Baggio had to score to keep his team alive. Under immense pressure, he uncharacteristically launched the ball high over the crossbar. The image of Baggio, hands on hips and head bowed, has become synonymous with football heartbreak. For Baggio, who carried Italy to the final almost single-handedly, it was a cruel end to a remarkable tournament.