Liverpool’s longest ever penalty shootout – 27 spot-kicks and one winner

Liverpool and Middlesbrough were tied at 2-2 after 120 minutes of their League Cup third round clash at Anfield on Tuesday, September 23, 2014. As it turned out, much of the drama was yet to come – as the sides embarked on a marathon penalty shootout that The Reds eventually won 14-13.

Plenty of shootouts will only need 10 spot-kicks to decide things, if that.

This one needed 30. That, in itself, tells a story.

A club record for both Liverpool and Middlesbrough and a new League Cup record. The three previous longest shootouts had each finished 9-8.

Over the course of 19 minutes, all 22 players who finished the match on the pitch took at least one penalty. Seven took two.


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Patrick Bamford – if including his equaliser from 12 yards in stoppage time at the end of extra time – took three.

What was impressive was the standard. 27 converted – 90pc success rate. Raheem Sterling – then 19 – was the only one of the 22 not to score within it.

Nerves were tested and they proved largely steely until Albert Adomah’s miss finally edged the Reds through in front of a delighted – and perhaps slightly worn out – Kop.

That last-gasp Bamford leveller felt a moment that the Teessiders were good value for.

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Aitor Karanka’s Championship side had gone toe-to-toe with Brendan Rodgers’ men for much of the evening. One that had started in fairytale fashion from a Liverpool perspective.

He decisively struck the ball first-time past Boro goalkeeper Jamal Blackman, who was stranded on the edge of his own box having kept out Rickie Lambert seconds earlier.

Things were thoroughly even from then on, though.

Lee Tomlin’s 25-yard drive stung the palms of Simon Mignolet on 37 minutes and Adam Reach then scored their first equaliser in the 62nd when he nodded home an enticing Grant Leadbitter free-kick.

They came closest to winning the tie in the 90 minutes, too.

Adam Clayton tested Mignolet from range in the 77th minute and then struck the top of the left-hand post in the 85th.

It would be the hosts who would retake the lead in extra-time, though.

A clever one-two between José Enrique and Adam Lallana down the left worked a crossing position for the former. Mario Balotelli very nearly converted in the six-yard box – but was denied by George Friend – before substitute Suso swept the loose ball home right-footed to give his side a 109th-minute lead. Another player scoring his first goal for the Reds.

Both Rossiter and Suso have gone on to establish themselves elsewhere in the years since.

The former – who has featured for Bury and Rangers – now captains League One Fleetwood Town, while the latter plies his trade in La Liga with Sevilla having had spells with Genoa and AC Milan in the meantime.

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Boro weren’t hanging about for sentiment, of course. As the second and final minute of stoppage time ticked down, Bamford was played into the box by former Reds defender Daniel Ayala.

Kolo Touré got across but only in time to bring the then Chelsea loanee down after he’d poked the ball into his stride. Penalty.

Bamford, who only came off the bench in the 111th minute, stepped up and duly swept the first of his three spot-kicks into the bottom-right corner – cuing a whole lot more of them down the other end.

After Balotelli had opened Liverpool’s account in typically composed fashion, Bamford actually had his next one saved.

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Boro only got back on level terms when Blackman denied Sterling – who would have put the Merseysiders through had he scored – and Jelle Vossen subsequently made it 4-4. Sudden death ensued. And ensued.

Each of the next 19 penalties – including one from each goalkeeper – were then scored, before Adomah sent his second of the shootout beyond the top-right corner.

It felt cruel for that moment to arrive, but it did, and it cued a solid cup run for the Reds.

Swansea City and AFC Bournemouth were beaten before Chelsea won the two-legged semi-final 2-1 on aggregate. A night that was worth going the distance for, nonetheless. One of quality and quantity.


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James Noble

Contributor. 20-year-old uni student studying sports journalism. Southern Red.

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