Liverpool's dramatic win over Middlesbrough makes it one of the longest shootout

The record for the longest penalty shootout came in 2005 when the Namibian Cup had to be settled by a record-breaking 48 spot-kicks.
In that game, KK Palace held their nerve to defeat the Civics 17-16 following a 2-2 draw in normal time.

Liverpool came out on top in a dramatic penalty shootout to beat Middlesbrough and progress to the fourth round of Capital One Cup on Tuesday night.

Their 14-13 victory after a 2-2 draw equalled an English record in professional football, but it still had some way to go to beat the longest on record.

The length of Tuesday's penalty shootout equals that of a 2011 Football League Trophy first-round tie between Dagenham & Redbridge and Leyton Orient.
On that occasion, 27 penalties were successfully converted before Orient defender Ben Chorley saw his second spot-kick saved by Dagenham keeper James Shea to hand the latter a 14-13 win.