Penalty shootouts often creates football’s most unforgiving moments. Reputations have been made or destroyed in these shootouts. History shows that it can also be the cruellest moment of all, one kick capable of haunting careers, defining legacies, and rewriting football folklore.

Here are 10 of the most painful penalty misses in football history, ordered by historical consequence and personal cost.

1. Roberto Baggio – 1994 World Cup Final

In the 1994 FIFA World Cup final between Italy and Brazil at the Rose Bowl, Pasadena, USA the match ended 0–0 after extra time. During the penalty shootout, Roberto Baggio missed Italy’s fifth penalty by shooting over the crossbar, allowing Brazil to win the shootout 3–2 and secure the World Cup.

2. Gareth Southgate – Euro 1996 Semi-Final

England faced Germany in the semi-final of UEFA Euro 1996 at Wembley Stadium. After a 1–1 draw, the match went to penalties. Gareth Southgate had his penalty saved, resulting in Germany winning the shootout and advancing to the final. Germany went on to win the tournament.

3. David Trezeguet – 2006 World Cup Final

The 2006 World Cup final between France and Italy finished 1–1 after extra time. In the shootout, David Trezeguet struck the crossbar with France’s second penalty. Italy went on to win the shootout 5–3.

4. John Terry – 2008 UEFA Champions League Final

The Champions League final between Chelsea and Manchester United ended 1–1 after extra time in Moscow. During the shootout, Chelsea captain John Terry missed a decisive penalty after slipping during his run-up. Manchester United won the shootout 6–5.

5. Stuart Pearce – 1990 World Cup Semi-Final

England played West Germany in the semi-final of the 1990 World Cup in Italy. After a 1–1 draw, the match was decided by penalties. Stuart Pearce missed his penalty, and England were eliminated after losing the shootout 4–3.

6. Kingsley Coman – 2022 World Cup Final

France and Argentina drew 3–3 after extra time in the 2022 World Cup final in Lusail. In the penalty shootout, Kingsley Coman had his penalty saved. Argentina won the shootout 4–2.

7. Aurélien Tchouaméni – 2022 World Cup Final

In the same shootout, Aurélien Tchouaméni missed France’s second penalty, shooting wide. His miss increased Argentina’s advantage in the shootout.

8. Mohamed Salah – 2022 World Cup Qualifying Play-Off

Egypt faced Senegal in a two-legged CAF World Cup qualifying play-off. After a draw on aggregate, the second leg in Dakar went to penalties. Mohamed Salah missed Egypt’s opening penalty, and Senegal qualified for the 2022 World Cup.

9. Jadon Sancho – Euro 2020 Final

The Euro 2020 final between England and Italy ended 1–1 after extra time at Wembley. In the penalty shootout, Jadon Sancho had his penalty saved. Italy won the shootout 3–2.

10. Brahim Díaz – 2025 AFCON Final

Most recently, In the Africa Cup of Nations final hosted in Morocco, the match went into extra time after a draw in normal time. Brahim Díaz missed a penalty during regulation time. Senegal later scored in extra time to win the tournament. (The Nation)