The 10 longest penalty shootouts of all-time - including Liverpool and Man Utd sagas

Sometimes even penalties are not enough to separate two teams.

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By now, you’ve probably scrolled past it a couple of hundred times on social media; that short clip of a goalkeeper celebrating wildly after saving a crucial penalty in a floodlit shootout, only for the devilish back spin on the ball to coax it agonisingly over the line as he sprints, clueless and ecstatic, out of frame.

The incident, milked as it has been by Football TwitterTM, happened on Thursday evening in a Europa League preliminary round clash between Northern Irish outfit Glentoran and Maltese visitors Gzira United, but by no means was it the only exceptional thing about the shootout.

By the time the face-off was concluded, Gzira had edged out their hosts in an epic saga that lasted for a colossal 28 spot kicks, with 27 of them finding the back of the net. That gargantuan tally comfortably puts it in the top 10 of the longest shootouts in recorded footballing history, but which other encounters make the list? Find out below...

10. Villarreal 11-10 Manchester United (22 penalties)

The 2021 Europa League final proved to be a thoroughly miserable evening for United goalkeeper David de Gea, who failed to stop a single one of Villarreal’s 11 penalties, and then saw his own effort saved by opposite number Geronimo Rulli.

That intervention gave the Spanish side a first major trophy in their history, not that being a footnote in such a sweet moment will have been any consolation to the Old Trafford number one.

9. Macclesfield Town 11-10 Forest Green Rovers (24 penalties)

Back in 2001, Macclesfield and Forest Green met in the first round of the FA Cup. So far, so normal. Fast forward to three-and-a-half hours of football and 24 spot kicks later, and this tie had quickly surpassed any kind of regularity.

In the end, it was the second efforts of first penalty-takers Keving Langan and Lee Glover that decided this one, with the former skying his attempt and the latter calmly stroking his home to set up a clash against Swansea City.

8. Brockenhurst 15-14 Andover Town (30 penalties)

A proper heavyweight clash from the Hampshire Senior Cup here, Brockenhurst and Andover broke the record for the most consecutive penalties scored in a English shootout before Town went and missed the 30th spot kick to decided proceedings. Nerves of steel.

7. Olympiacos 15-14 AEK Athens (30 penalties)

A near identical situation to Brockenhurst and Andover’s titanic struggle, although this one happened in a Greek Cup final between two of the biggest sides in the country. After extra time the scores were tied 4-4, which in and of itself made this one a classic, but little did spectators know that the drama was only just beginning.

Twenty-nine penalties dispatched, one missed, and the winning moment was provided by silver fox goalkeeper Antonis Nikopolidis. Absolutey iconic.

6. Liverpool 14-13 Middlesbrough (30 penalties)

Thirty penalties. That magic number again. Back in 2014, when the Carabao Cup was still called the Capital One Cup, Middlesbrough very nearly gave a bloody nose to Brendan Rodgers’ Liverpool when Patrick Bamford struck in injury time to drag the Merseysiders to extra time and penalties. In the end, it was Albert Adomah who missed and sent Boro crashing out.

5. Scunthorpe United 14-13 Worcester City (32 penalties)

By no means was that the longest English shootout that year though. Nope, that accolade went to Scunthrope and Worcester, who played out a 32-kick slugfest in the FA Cup - the longest in the competition’s history.

And nobody was more relieved than Iron striker Miguel Llera, who missed his first penalty before firing in the winner on his next time around after City’s Wayne Thomas saw his effort saved.

4. Netherlands U21 13-12 England U21 (32 penalties)

Lengthy shootouts are not just the preserve of senior football, it would seem. Way back in 2007, England’s U21 side were embroiled in a tense struggle with the Netherlands that ultimately had to be settled from 12 yards.

In typical English fashion, the Young Lions crashed out of semi-finals of the European Championships after Anton Ferdinand cannoned his effort off the crossbar, but not before an awful lot of other kicks were taken.

3. Old Wulfrunians 19-18 Lane Head (44 penalties)

Really upping the ante here with some non-league action from the Midlands. This JW Hunt Cup tussle was, for a short while, the lenghtiest shootout in English history, and came following a 3-3 draw after extra time. In the kind of pleasing detail that only amateur football can deliver, the deciding kick was scored by left-back Jack Marsh, a teacher by trade and the son of Old Wulfrunians club secretary, Simon.

2. KK Palace 17-16 Civics (48 penalties)

We’re off to Namibia for this one, a nation known for its wildlife, diamonds, and a never-ending 2005 domestic cup final penalty shootout.

You might think that there is some kind of misprint in the sub-heading here. After all, how can 48 penalties produce just 33 goals? Well, dear reader, the short answer is that 15 of them were utterly abysmal. Still, if we’re going on number of penalties and number of penalties alone, this one slots in comfortably at number two.

1. Washington 25-24 Bedlington (54 penalties)

And finally, the distinction for the longest penalty shootout in footballing history goes to two non-league clubs from the North East of England. Just 40 people were in attendance to witness Washington player Bedlington in the Ernest Armstrong Memorial Cup last year, but they certainly got their money’s worth out of this one.

Fifty-four spot-kicks were needed to split the sides, easily beating the previous record set in Africa almost two decades prior.