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, 5-4, 4-2 etc. 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 entertainment.

90min here takes a look at five of the longest penalty shootouts to ever take place.

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.

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.

The 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 Mitroglu and Matt Derbyshire in action for Olympiacos. Kostas Manolas and Juanfran were in the AEK Athens squad.

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.

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.

The record for the longest penalty shootout was actually only broken 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.

The previous record according to Guinness was 48 attempts, so the two sides were comfortably clear.