The longest penalty shootouts ever

Penalty shootouts are the cruellest way to decide a football match, especially given they tend to be in the latter stages of a tournament. There's no denying that they're incredible entertainment if your team isn't in it, though.

That entertainment (or agony) gets even greater if you start to get beyond the classic scorelines of 4-3 and 5-4. Sudden death is where the pressure really ramps up and where the nerves really start to show.

If you get through all of that sadistic fun and there still isn't a winner, we're into the territory of goalkeepers taking penalties against each other. The height of football pleasure.

Here are the longest penalty shootouts on record.

10. Liverpool 14-13 Middlesbrough - 30 penalties

The Capital One Cup (now Carabao Cup) saw a ridiculously long penalty shootout back in 2014 between Liverpool and Middlesbrough.

An injury-time goal from a young Patrick Bamford meant the teams were tied after 120 minutes. 30 penalties later, Albert Adomah missed and Liverpool went through to the fourth round.

It was a Liverpool side coached by Brendan Rodgers and featuring the likes of Kolo Toure, Jordan Rossiter, Raheem Sterling, Lazar Markovic and Rickie Lambert. Grant Leadbitter and Daniel Ayala could be seen for Middlesbrough, along with a young Ryan Fredericks.

9. Olympiacos 15-14 AEK Athens - 2009

The most dramatic shootouts come when it's a cup final, and the Greek Cup final in 2009 between Olympiacos and AEK Athens was a barnstormer.

Extra time ended 4-4, which is good enough, but the following shootout ended 15-14 to Olympiacos and the winning penalty came from the goalkeeper, Antonis Nikopolidis. Does it get any better than that?

Fans were lucky to see the likes of Olof Mellberg, Kostas Mitroglou and Matt Derbyshire in action for Olympiacos. Kostas Manolas and Juanfran were in the AEK Athens squad.

8. Brockenhurst 15-14 Andover - 30 penalties

Barring the incredible number of penalties, what makes this tie stand out is the fact that not a single one was missed before the final kick which decided the game.

29 perfect spot kicks meant the record was broken for consecutive penalty shootout goals in England. It was a Hampshire Senior Cup match for the ages.

7. Worcester City 13-14 Scunthorpe - 32 penalties

When you picture penalty shootout drama, the FA Cup may well be what springs to mind. In fact, the seventh longest shootout ever recorded came in the second round of the competition in 2014.

After a 1-1 draw, non-league Worcester were desperately searching for a spot in the third round of England's oldest cup competition but had to overcome League One Scunthorpe.

Unfortunately for the minnows, it was Scunthorpe who prevailed in a 32-kick shootout, with Miguel Llera making amends for missing his first penalty by smashing home a second that secured victory.

6. Netherlands U21s 13-12 England U21s - 32 penalties

England's penalty woes have been well documented but the senior side have arguably never experienced as brutal a shootout as the Under-21s did at the 2007 European Championship.

In their semi-final clash with the Netherlands, 32 penalties were taken before Anton Ferdinand missed the decisive kick. Heartbreak for the young Lions, who had to watch the Dutch claim the title just a few days later.

Just to make us all feel old, James Milner, Ashley Young, Mark Noble and Scott Carson were among those to score for England - with the former three actually netting twice each in the shootout.

5. Preston 16-15 Fulham - 34 penalties

We have already seen the Carabao Cup's ability to cause chaos in penalty shootouts, with the competition's decision to bin extra time in the earlier rounds only enhancing the dramatics from 12 yards.

After Middlesbrough had fallen agonisingly short against Liverpool previously, it was Fulham's turn to feel the pain in 2024. The Cottagers were defeated 16-15 by Championship Preston North End after 34 penalties were taken at Deepdale.

Amazingly, only three were not scored, with Timothy Castagne missing the crucial kick late into the evening.

4. Old Wulfrunians 19-18 Lane Head - 44 penalties

"After the 22nd penalty I went to get the team's fish and chips. But, when I got back, the shootout was still going," said Simon Marsh, the father of one of Old Wulfrunians' penalty scorers.

Indeed, it was a long old night in the JW Hunt Cup between two lower-level sides from the Midlands. The shootout commenced after a 3-3 draw across regulation time and took nearly half-an-hour to complete.

You've got to love grassroots English football, eh?

3. KK Palace 17-16 Civics - 48 penalties

The Namibian Cup Final may not be on everyone's radar, but it was the place to be in 2005 as 48 penalties were taken by KK Palace and Civics.

You'd be right in thinking that that's a lot of penalties for the scoreline. They missed 15 of them, which is why it went on for so long following the 2-2 draw in extra time.

2. Washington 25-24 Bedlington - 54 penalties

The previous record for the longest penalty shootout was actually only set in 2022 and was done so in the United Kingdom.

54 penalties were needed to separate non-league sides Washington and Bedlington in the Ernest Armstrong Memorial Cup. The crowd of 40 were treated to a dramatic 3-3 draw in the 90 minutes before Washington prevailed 25-24.

1. SC Dimona 23-22 Shimshon Tel Aviv - 56 penalties

The 2022 world record lasted for just two years before being stolen by Israeli sides SC Dimona and Shimshon Tel Aviv in May 2024. In their semi-final promotion play-off, both teams took an incredible 28 kicks before the shootout was settled.

Dimona had already produced a stoppage-time equaliser to send the game to extra-time and subsequently penalties, and it was the hosts who ran out victors in a remarkable shootout.

There were a fair few misses - with Washington and Bedlington scoring more of their 54 penalties - but there's no doubt that it's the longest shootout ever recorded.

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