Chelsea loanee had epic Liverpool battle in only Middlesbrough outing: View | OneFootball

Jamal Blackman made just one appearance for Boro, but he was involved in an unbelievable penalty shootout.

Middlesbrough's 2014/15 EFL Cup run never truly took off, however, it was memorable for another reason.

In a season that culminated in a Championship Play-Off final defeat to Norwich City at Wembley, there were a lot of standout stars.

Grant Leadbitter, Kike and Patrick Bamford all played a huge role in Boro's success that season, but one player that played a part in one of the most bizarre nights in the club's history was Jamal Blackman.

The then 20-year-old made the move to the Riverside on loan from Chelsea in August 2014, with his deal expected to last until the end of January. However, he made just one appearance on Teesside, and his loan was cancelled by the team who won the Premier League that season.

Nevertheless, the game that he did play in turned out to be one that perhaps lasted a lot longer than anybody would have expected that night.

Liverpool and Middlesbrough played out 120 minutes of end-to-end drama in 2014 EFL Cup clash

Middlesbrough enjoyed a fairly routine route to the third round of the League Cup in 2014/15, easing past League One Oldham Athletic in a 3-0 win away from home, before beating Preston North End 3-1 at the Riverside Stadium.

They were drawn against Liverpool in the next stage, as the team who had finished 2nd in the Premier League the season prior entered the competition.

The two sides had not met since February 2009, with Boro running out 2-0 winners at home, but it was a different test five years later.

The top flight club, who were being managed by Brendan Rodgers at the time, put out a much weakened squad compared to their usual side, but Blackman still had to try and keep out Adam Lallana, Raheem Sterling and Rickie Lambert, as well as Mario Balotelli, who came off the bench.

Liverpool took the lead early through Jordan Rossiter after Blackman and his defender Kenneth Omeruo mis-communicated, allowing the Reds' academy graduate to strike from distance, with his shot flying under the legs of the goalkeeper.

Adam Reach equalised for Boro just after the hour mark, heading in from a Leadbitter free-kick, taking the game to extra-time.

A 109th minute strike from Suso, who now plays his football for Sevilla, looked like it was going to take the Merseyside team through to the fourth round, but there was another twist.

Kolo Toure brought down Bamford in the box with just a minute left of extra-time, and the other Chelsea loanee from that season equalised with the final kick of the game.

Jamal Blackman took part in a penalty shootout classic in only Middlesbrough appearance

Although the game itself was hectic and full of drama, it had nothing on the consequential penalty shootout.

After scoring from the spot in extra-time, Bamford missed Middlesbrough's first in the shootout itself with his effort stopped by Simon Mignolet.

Sterling had the opportunity at 4-3 to win the tie, however, Blackman was equal to the future Manchester City star's spotkick, allowing his side the chance to level things up, which they did.

In total, 30 penalties were taken between the two sides, a record at the time. Derby County and Carlisle United broke it two seasons later, before Preston North End and Fulham took the record in the third round of the 2024/25 edition of the competition, taking 34 penalties to decide a winner.

Suso scored to make it 14-13, before Albert Adomah fired wide at the Kop End of Anfield to end the tie in the most dramatic of circumstances.

The Chelsea loanee, Blackman, scored a penalty of his own, and although he managed to keep one out, it proved to be one of his final acts in a Middlesbrough shirt.

He was recalled by the Blues early in January 2015, to act as the third-choice goalkeeper due to the sale of Mark Schwarzer to Leicester City, and he couldn't get in the Boro team anyway in league action, with the experienced Dimitrios Konstantopoulos ahead of him in the pecking order - a position he would never relinquish.

Despite his involvement at the club being extremely little, Blackman will probably never forget it due to that shootout at Anfield.