Liverpool required an extraordinary penalty shootout to finally see off the challenge of Middlesbrough and stay alive in the Capital One Cup. In what was the longest shootout in League Cup history, just two kicks were missed by both teams as goalkeepers stepped up and scored and several players found the net twice before Albert Adomah became the unfortunate man to miss and leave Liverpool as 14-13 victors.

Middlesbrough had refused to go down lightly throughout the League Cup third round clash at Anfield and twice came back from a goal down. First Adam Reach’s second-half strike cancelled out an early debut goal from Liverpool’s 17-year-old debutante Jordan Rossiter to force extra time. Liverpool appeared to be heading through when Suso came off the bench to score 11 minutes from the end of extra time. Instead, Kolo Toure foolishly brought down Patrick Bamford deep into injury time and the on loan Chelsea forward picked himself off to improbably send the contest to penalties, where even greater drama was to come.

The result will come as considerable relief for manager Brendan Rodgers as he avoids overseeing a fourth defeat in six matches, but there will be substantial frustration, too, at having been extended an extra 30 minutes and them some ahead of the Merseyside derby on Saturday. While Rodgers rested captain Steven Gerrard, he still fielded first-teamers like Raheem Sterling, Adam Lallana, Simon Mignolet and Mamadou Sakho, while Mario Balotelli was required off the bench.

There was a first start for Rickie Lambert up front and the former Southampton man was involved in helping set up a goal for another debutante just 10 minutes in, when it looked like being a comfortable night for the Premier League outfit. While the youngster hailed by many as the next Gerrard claimed a moment he will never forget, it was a comedy of errors in the Middlesbrough back line that gifted Liverpool the lead. A mix up between defender Kenneth Omeruo and his goalkeeper allowed Lambert a strike that Jamal Blackman repelled but when Rossiter sent a fairly tame shot back in from more than 30 yards, Blackman swung and missed with an attempted block with his legs.

It was the defensive problems of Liverpool that later took the focus, however. After successive Premier League defeats to Aston Villa and West Ham that featured the concession of set-piece goals, Liverpool showed they had yet to put things right. The hosts looked to be heading safely through until the 62nd minute when Grant Leadbitter’s excellent free-kick saw Jose Enrique miss a clearance and Reach head past Mignolet from close range.

Both sides had chances in the final 10 minutes to win the tie in normal time. Adam Clayton struck the outside of the post before Liverpool were denied a penalty after a strong claim for handball in the box. Instead, Liverpool were taken to a most unwanted period of extra time against a visiting team managed by former Real Madrid assistant coach Aitor Karanka and that had won three straight league games.

Middlesbrough’s challenge looked to be ended when Suso drilled low through a crowded penalty area just 11 minutes coming on for his first Liverpool appearance in 16 months. Instead Rodgers’s men again committed defensive suicide. Sterling started the disaster by gifting the ball to former Liverpool youngster Daniel Ayala and then Toure clumsily brought down Bamford in the area.

Having scored from the spot to force penalties, Bamford then missed Middlesbrough’s first in the shootout. The next six were scored to give Sterling the chance to win it, but Blackman came up with his first save to force sudden death. Incredibly the next 20 were scored until Adomah stepped up for the second time and on this occasion put his effort wide of the post to allow Anfield to finally exhale.

Liverpool  2(14-13)2 Middlesbrough All Goals... by yarigavideo