Five longest penalty shootouts in professional football

Some iconic face-offs stretched extremely long in order to decide a winner.

One of the most exciting prospects of a football game are the penalty shootouts. When two teams are level at the end of regulation and added time in a match, a penalty shootout between the sides ensues to declare a winner. No matter what level, a penalty shootout is equally nerve-wracking for the fans and the players. Initially, each team takes five spot-kicks, but in some occasions, even the five regulatory spot-kicks aren’t enough to find a winner.

The shootout can stretch indefinitely until one of the two teams scores/misses the deciding penalty kick. Sometimes, that can compel even the goalkeepers to take a spot-kick or the outfield players to retake their penalties once all the 11 players have executed their turns in the shootout.

On May 26th, 2021,in the Europa League finals, Villarreal won a marathon penalty shootout against Manchester United by 11-10 which reminded us of several marathon shootouts over the years. 

We have compiled a list of one of the longest penalty shootouts that stretched out way beyond the first five spot-kicks in order to declare the winner. Here are five of the longest penalty shootouts in football.

Netherlands U-21s 13 - 12 England U-21s

In 2007, while facing each other in the U-21 European Championships, developmental sides of European giants in Netherlands and England faced off and it took 32 spot-kicks to decide a winner at the end.

Some of the notable players that took part in this goal-fest were Ashley Young, James Milner, and Anton Ferdinand (who missed the deciding penalty) on England’s team while the Netherlands had Ryan Babel, Royston Drenthe and Gianni Zuiverloon among others.

Scunthorpe United 14 - 13 Worcester City

The current FA Cup record for the longest penalty shootout is held by Scunthorpe and Worcester City when their second-round fixture game could not be decided in regulation time.

The epic shootout saw League One side Scunthorpe United emerge victorious over non-league Worcester City after 32-spot-kicks as they moved forward into the third-round.  

https://youtu.be/UZZ3LBrfhf8

Liverpool FC 14 - 13 Middlesborough

Back in 2014, when the EFL Trophy was known as the Capital One Cup, Liverpool faced a valiant Middlesborough in the third round of the competition. The match was undecided in the regulation time and therefore needed to be settled by a penalty shootout.

Incredibly, Rickie Lambert was again involved in an epic penalty shootout that took 30 spot-kicks in front of the Kop End to decide a winner. The Red marched into the fourth round after Albert Adomah of Middlesborough missed his penalty.

https://youtu.be/cugBAUAJfrU

Olympiacos 15 - 14 Aek Athens

In the Greek Cup final back in 2009, two of the Greek football giants in Olympiacos and AEK Athens clashed and were inseparable. The match saw both sides finish on equal terms with scoreline at 4-4 after the regulation and extra-time where penalties were required to decide a winner of the competition.

After what ensued was an epic shootout, and was finally won by Olympiakos when goalkeeper Antonis Nikopolidis fired home the winning penalty after saving the penalty hit by the opposition custodian.

https://youtu.be/uF0WYo9qVNg

KK Palace 17 - 16 The Civics

The world record for the longest penalty shoot-out in a professional football game happened back in 2005 when KK Palace and The Civics clashed in the Namibian Cup.

After a 2-2 draw in the regulation time and no winner was found after the extra time, the winner was decided after a marathon 48-kick penalty shootout.

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