Preston North End’s shootout victory over Fulham last night in Round Three of the Carabao Cup was a landmark moment for the competition.

Here, we take a look at the list of longest penalty shootouts in the history of the League Cup:

Preston North End 16-15 Fulham

17 September 2024

Last night, history was made as Preston North End and Fulham played out the longest-ever penalty shootout in the existence of the competition. A total of 34 spot kicks were taken – 31 of which were successfully converted – as Paul Heckingbottom’s men booked their place in Round Four of the Carabao Cup.

It all came down to sudden death and Lilywhites midfielder Ryan Ledson – who made the score-sheet for the home team in a 1-1 draw at Deepdale after 90 minutes – scored the decisive penalty after Fulham’s Timothy Castagne cleared the bar with his effort just moments before.

Derby County 14-13 Carlisle United

24 August 2016 

It was a night to remember for Derby County academy graduate Timi Max Elsnik who helped the Rams to secure passage to Round Three. On his first team debut for the Club, the 18-year-old – one of six Derby and Carlisle United players to take two turns in the shootout – slotted home the winning spot kick for Paul Clement’s side.

Mike Jones’ injury time equaliser for the Cumbrians forced the tie to penalties in 1-1 draw at Pride Park. A further five penalties were missed – with 32 taken in total – to set a new record for the longest shootout in League Cup history which would stand for eight years.

Liverpool 14-13 Middlesbrough

23 September 2014 

Liverpool advanced to Round Four after beating Middlesbrough 14-13 on spot kicks in a record-equalling penalty shootout. The game between the Merseysiders and the North Yorkshire team ended in a 2-2 draw after Patrick Bamford levelled proceedings in 30 minutes of additional time.

It took 30 penalties – 27 of which were scored – to separate the two teams. In the end, Albert Adomah’s miss for Boro edged it for Brendan Rodgers’ Reds at Anfield. The contest matched the record for the highest-scoring shootout in English football, rivalled only by Dagenham & Redbridge vs Leyton Orient in the EFL Trophy in August 2011.

Accrington Stanley 11-12 Tranmere Rovers

9 August 2022

Tranmere Rovers came from 2-0 down against Accrington Stanley to overcome the Lancashire team on spot kicks. Micky Mellon’s Tranmere came our fighting in the second half, completing the comeback in the 93^rd minute courtesy of an own goal with the last kick of the game.

And the visitors won 12-11 in the shootout with a total of 26 penalties taken. Both stoppers – Rovers’ Mateusz Hewelt and Stanley’s Lukas Jensen – produced saves, with Hewelt keeping out the final kick from Shaun Whalley as Tranmere went through to Round Two.

Accrington Stanley 11-10 Bradford City

9 August 2016

Accrington were involved again back in August 2016 when the Club kicked off their 2016/17 League Cup campaign at home to Bradford City in Round One. A goalless stalemate called for penalties and 24 kicks were taken as Stanley saw off the League One Bantams in the shootout.

Stanley’s Barnsley-born midfielder Jordan Clark was the hero for the hosts – who were reduced to 10 men during the game following the dismissal of goalkeeper Elliot Parish – as he kept his nerve to convert the decisive penalty after Bradford’s Reece Webb-Foster spurned his spot kick.

Bournemouth 11-10 Crystal Palace

15 September 2020

 Similarly, 24 penalties were taken between Bournemouth and Crystal Palace when the Championship Cherries beat Premier League Palace on spot kicks during the 2020/21 season to seal their place in Round Three.

Both keepers stepped up as Palace’s Wayne Hennessey denied Bournemouth’s Asmir Begovic, only for Hennessey to then fail to hit the target. However, Bosnia and Herzegovina international Begovic redeemed himself shortly after when he saved from Eagles midfielder Luka Milivojevic to win it.

Chelsea 10-11 Liverpool

27 February 2022

The stakes were high for Chelsea and Liverpool when the two league rivals went head-to-head in a penalty shootout under the famous Wembley arch in the 2022 Carabao Cup Final. Neither team had been able to find a way through after 120 minutes of football, which ended goalless and there was no quick resolution on spot kicks, either.

Of the 22 penalties taken, 21 were scored. Liverpool keeper Caoimhin Kelleher – a prolific striker during his early youth career – rippled the net with the second to last kick. However, with the showpiece on a knife edge, Chelsea stopper Kepa Arrizabalaga – who was substituted on late in added time – blasted his effort over the bar as Jurgen Klopp’s Reds won the competition for a record ninth time.

Nottingham Forest 10-9 Bury

14 August 2018

League Two side Bury almost caused an upset in Round One in August 2018 against Nottingham Forest who almost fell at the first hurdle. The Shakers took an early lead before Matty Cash popped up with a last gasp leveller.

Bury defender Eoghan O'Connell – who netted the opener for the visitors in the opening two minutes of the game – saw his spot kick saved by Forest’s substitute keeper Luke Steele, who came on after fellow gloveman Jordan Smith received a straight red card in the first half, to signal the final whistle, 22 penalty kicks later.

Arsenal 9-8 Rotherham United

28 October 2003

Last but certainly not least, Arsenal progressed 9-8 on penalties against Rotherham United at Highbury. On the same night that Cesc Fabregas became the Gunners’ youngest-ever player, aged 16, 22 spot kicks were taken – 11 by each team. Darren Byfield restored parity in the 90^th minute meaning Arsene Wenger’s side had to do it the hard way.

Gary Montgomery filled in between the sticks after Millers keeper Mike Pollitt was sent off for handball in extra time. However, the pressure got to Rotherham’s Chris Swailes when he had his effort saved and Sylvain Wiltord, who missed his first penalty, scored at the second time of asking to secure passage to Round Four.