In all of sports, there is no moment as tense or high pressure as a penalty kick. This is particularly true during the dreaded penalty shootouts, where all of a sudden the spotlight is thrust onto one player who must beat the goalkeeper from 12 yards. A miss can be devastating and let the entire team down, and sometimes even an entire nation. Some penalty misses have been so heartbreaking that the player has never fully recovered from the miss, and no amount of comfort from teammates was able to console these players who were unable to hold their nerve.

10. Landon Donovan v Real Salt Lake (2009 MLS Cup)

Landon Donovan is somewhat the poster boy of the MLS, having won a record 6 MLS cups and being the all-time leader in goals and assists. He was crowned the 2009 MLS MVP and also scored the goal of the season, but this is all overshadowed by an uncharacteristic wobble in the 2009 MLS Cup against Real Salt Lake. The game went to penalties after a 1-1 draw, and everyone expected the MVP to convert like he normally does as he stepped up to take L.A’s 4th penalty. He struck with confidence, but his effort sailed over the bar and underdogs Real Salt Lake would go on to win 5-4 leaving the entire football world in shock. He would lift the trophy in 2011, 2012 and 2014, but this miss will no doubt stick in the back of his mind and showed that Donovan is, in fact, human after all.

9. Marco Van Basten v Denmark (Euro 1992)

After Holland scored a late goal to make the score 2-2 in the Euro 1992 semi-finals against Denmark, the game would go on to extra time and then penalties. Marco Van Basten, the FIFA World Player of the Year, stepped up to take Holland’s second penalty and the entire world fully expected him to convert. He attempted to tuck the ball in the bottom corner, but Denmark’s Peter Schmeichel got down quickly to make a fine save. It would be the only penalty miss. Denmark advanced to the finals 5-4, where they would then lift the trophy after defeating Germany 2-0 in the final. Van Basten had dominated the competition four years earlier and guided Holland to victory as top scorer and player of the tournament, including a stunning volley in the final against the Soviet Union.

8. Chris Waddle v West Germany (1990 World Cup)

England are a team that are famously cursed when it comes to penalties, having been knocked out of several major tournaments in the cruelest manner and with several high profile misses (more on a few of these later). It all began in the 1990 World Cup semi-finals against Germany, and things started off well with the Three Lions converting their first three penalties. Stuart Pearce was up next, but his effort was saved by the keeper’s legs, and after Germany converted their next penalty it meant that Chris Waddle had to score to keep England’s hopes alive. Waddle blasted his shot over the bar, and Germany advanced to the finals where they would beat Argentina. It marked the beginning of a long and ongoing curse for England, and the entire nation now dreads any competition going to penalty kicks with confidence remaining so low from 12 yards.

7. Andriy Shevchenko v Liverpool (2005 Champions League Final)

In one of the most stunning comebacks of all time, the 2005 Champions League final is a match that all soccer fans will remember. It is one of the greatest moments in Liverpool’s history, but it is certainly an evening that Andriy Shevchenko and A.C. Milan will not look back on too fondly. After taking a commanding 3-0 lead in the first half, it appeared that the final was all but over. Liverpool then shocked the entire world by scoring three goals in the space of six minutes, sending the game into extra time and then on to penalties. The enormous momentum shift had clearly had an impact on the A.C. Milan players, and with the penalty scoreline at 3-2 it was down to Shevchenko to keep their hopes alive. He would send his effort straight down the middle and it was easily saved, completing an astonishing comeback win for Liverpool.


6. Gareth Southgate v Germany (Euro 1996)

During Euro 1996, England were hoping to change their fortunes and felt confident being the hosts of the competition. They had a fantastic march to the semi-finals, and were on the verge of making their first final since they famously won the 1966 World Cup, which they also hosted. First they had to beat a quality German side, and there was nothing to separate the teams after 120 minutes. Tension mounted as both sides converted their five penalties, sending it to sudden death. England defender Gareth Southgate stepped up to take the sixth, but his low effort was kept out by Andreas Kopke. Germany’s Moller then scored and sent them through to the finals where they would win. It was more agony from the penalty spot for England, with Southgate inconsolable after the miss. Southgate is now manager of the England U21 squad, where penalties are surely practiced often.

5. Asamoah Gyan v Uruguay (2010 World Cup)

During the 2010 World Cup, Ghana had an impressive march to the quarter-finals where they faced Uruguay. They would come agonizingly close to reaching the semis, but a famous penalty miss and a controversial moment from Luis Suarez saw Ghana suffer a heartbreaking loss. With the score at 1-1 after 90 minutes, play went to extra time where Suarez intentionally blocked an effort on goal with his hands. He was sent off and Ghana were awarded a penalty at the death of extra time. Asamoah Gyan took on the responsibility, but his effort would cannon off the crossbar much to the dismay of Gyan and his teammates (Suarez was seen celebrating on the sidelines). The momentum had shifted going into the penalty shootout, and despite Gyan converting his effort, it would be Uruguay who prevailed 4-2. Suarez later controversially stated “the ‘Hand of God’ now belongs to me.”

4. David Beckham v Portugal (Euro 2004)

Yet another heartbreaking penalty miss for England, and another miss that would see them exit from a major international tournament. With 120 minutes not enough to separate the two teams in a fascinating match that ended 2-2, it was once again a dreaded penalty shootout for England. First up was Captain David Beckham, who had missed his previous two penalties for the Three Lions (including one earlier in the competition). This may have plagued his thoughts as he took the penalty, as he appeared to slip and missed the entire goal by some distance. It was the worst possible start for a team with low confidence in penalty shootouts, and Portugal went on to win 6-5. Once again the team and the entire nation at home were devastated and denied in the cruelest possible manner.

3. David Trezeguet (2006 World Cup Final)

The 2006 World Cup Final between France and Italy is perhaps best remembered for Zinedine Zidane’s moment of madness where he headbutted Marco Materazzi in extra time, an incident which somewhat tarnished his reputation in his final game. With the score at 1-1 after 120 minutes, it would be a penalty shootout to determine who would be world champion. With the shootout score at 2-2, France’s David Trezeguet may have felt the immense pressure and fired his effort off the crossbar much to his own shock, as well as the entire nation of France watching back at home. He would be the only player not to convert, seeing Italy lift the trophy after a tense, dramatic and eventful final. Luckily for Trezeguet, Zidane’s shocking headbutt is often what is remembered from this final and many wonder what would have been had Zidane been on the pitch.

2. John Terry v Manchester United (2008 Champions League Final)

A penalty miss that will still haunt Jason Terry to this day, not even the Moscow rain could hide the Chelsea captain’s tears during the 2008 Champions League final against Manchester United. After the match finished 1-1, the all-English final went to penalties to decide the champion. After Ronaldo missed his penalty, Terry stepped up with the opportunity to win his first ever CL title, but he would slip as he took the pitch and struck the outside of the post. The shootout went to sudden death, and teammate Nicolas Anelka would also miss to see United claim the title in an unforgettable final. Terry has admitted he still thinks of the miss at night, but his pain would be somewhat relieved following Chelsea’s 2011/12 Champions League victory over Bayern Munich which also went to penalties (Terry did not feature due to suspension).

1. Roberto Baggio v Brazil (1994 World Cup Final)

The most heartbreaking miss in soccer history. There is no bigger platform than the World Cup final, and this miss is often what Roberto Baggio is best remembered for despite being one of the all-time greats. Italy faced Brazil in the 1994 World Cup final, and managed to reach this stage largely thanks to the excellent play of Baggio, who had five goals in the competition. The final would go to penalties (for the first time ever), and Baggio stepped up, needing to score to keep his team (and entire nation’s) hopes alive. The immense pressure on Baggio surely played a part in his miss, as he would sky his effort over the bar much to the delight of the Brazilian side, and the dismay of his teammates. It is an incredibly harsh and cruel way to lose a World Cup final, and no doubt mentally scarred Baggio for life.