Liverpool triumph 14-13 against Middlesbrough after a staggering 30 spot-kicksTuesday night's Capital One Cup Round 3 action saw a record-breaking penalty shoot-out end 14-13 to Liverpool against Middlesbrough after 30 spot-kicks.
The previous longest shoot-out in the League Cup was a 9-8 scoreline on three occasions, most recently between Arsenal and Rotherham in 2003, but that was smashed under the lights at Anfield following a 2-2 draw after 120 minutes of action.
Both sides missed one of their first five but, from then on, it was a penalty masterclass with the next 19 hitting the back of the net, including strikes from Boro goalkeeper Jamal Blackman and Liverpool stopper Simon Mignolet.
Some 17 minutes after the first penalty had been taken, Boro's Albert Adomah became the unfortunate player to bring the tie to an end, blasting his attempt from 12 yards into the Kop to leave the score 14-13 in favour of the hosts.
The result equalled the record shoot-out scoreline in English professional football, which was set by Dagenham & Redbridge and Leyton Orient in the Johnstone's Paint Trophy in September 2011, although that game saw 28 penalties taken, two fewer than Tuesday's thriller.
England's Under-21s were also involved in a mammoth shoot-out in the 2007 European Championships, losing 13-12 to Holland after 32 penalties.
However, the longest penalty shoot-out of all time saw a staggering 48 spot-kicks taken in the 2005 Namibian Cup Final between KK Palace and Civics, with the former winning 17-16.