In 2014, who did Liverpool beat 14-13 in the longest League Cup penalty shoot-out?

Liverpool beat Middlesbrough after 30-penalty League Cup shoot-out.

When it was all over, 27 of 30 penalties had been converted, Middlesbrough were on their knees in despair and Liverpool were too shattered to indulge fully in celebration. One of the most remarkable shoot-outs in English history brought relief for Brendan Rodgers’ team as they edged into the fourth round courtesy of an exhausting finale at Anfield and one final miss from the unfortunate Albert Adomah.

The Middlesbrough winger sliced the 30th and final spot-kick into the Kop to settle a seemingly never-ending tie at 10.42pm. Both teams had gone through the card in the shoot-out, goalkeepers included, with Patrick Bamford, whose penalty in extra-time stoppage time carried the Championship club so far, and Raheem Sterling having efforts saved before Adomah’s miss.

It was the longest penalty shoot-out in the history of the League Cup, the previous record set at 9-8 on three occasions, and more extensive than the FA Cup’s highest total when Macclesfield beat Forest Green 11-10 in 2001.”