The Most Extraordinary Penalty Shootouts in Football History

When football historians look back at the strangest and most extraordinary penalty shootouts of all time, England’s dramatic victory over Sweden at Euro 2025 will surely top the list.

Of the 14 penalties taken that night in Zurich, only five were scored, six were saved, and three were completely missed. BBC pundit Ellen White described it perfectly: “Terrifying watching.”

While modern football analytics have reduced the idea of shootouts being a “lottery,” nothing can fully account for the pressure players face on the spot. As Alan Shearer once quipped after England’s men won a shootout at Euro 2024: “Pressure is for tyres.”

Here’s a look at some of the most memorable – and bizarre – penalty shootouts ever:

Miss, Miss, Miss…

At Euro 2025, England became the first team in Women’s Euros history to miss three consecutive penalties in a shootout and still progress. The conversion rate? Just 36% – the worst ever at the tournament.

For comparison, consider:

• 1986 European Cup Final: Barcelona lost 2-0 to Steaua Bucharest after all four of their penalties were saved.

• 2020 Japanese Super Cup: Vissel Kobe beat Yokohama Marinos 3-2 in a shootout where nine penalties in a row were missed.

• 1985 Finnish Cup Final: Haka and HJK combined for seven straight misses before Haka finally triumphed.

Even Sweden’s keeper Jennifer Falk, who saved four penalties in Euro 2025, ended up missing the decisive spot-kick herself.

On, and On, and On…

Sometimes shootouts go on so long they feel like they’ll never end.

• 2024 Liga Alef Playoffs: FC Dimona beat Shimshon Tel Aviv 23-22 after an incredible 56 penalties.

• 2023 Women’s World Cup: Australia edged France 7-6 after 20 penalties – the longest in World Cup history.

• EFL Trophy 2024: Aston Villa U21s beat Blackpool 18-17 in a shootout where 31 consecutive penalties were scored before the first miss.

Fans of Liverpool and Manchester United will remember:

• Liverpool’s 14-13 win over Middlesbrough (2014).

•  United’s agonizing 11-10 loss to Villarreal in the 2021 Europa League Final, with David de Gea missing the decisive kick.

The Most Controversial Shootout Ever?

One contender is Orlando City vs New York City FC in the 2020 MLS Playoffs:

• Orlando keeper Pedro Gallese saved what he thought was the winning penalty… only for VAR to rule he’d stepped off his line.

• Gallese was then sent off, and a defender (Rodrigo Schlegel) had to go in goal.

• Schlegel became the unlikely hero, saving NYCFC’s seventh penalty before Orlando finally won 6-5.

• Total time for the shootout? 21 minutes and 35 seconds.

Conclusion

From chaotic misses to marathon duels, penalty shootouts provide football’s most nerve-shredding drama. Whether it’s England’s Euro 2025 triumph or Orlando City’s surreal MLS win, these moments live forever.