Liverpool entered the League Cup semi-finals for a record 17th time and 17-year-old Ben Woodburn entered the record books. The Wales Under-19 international eclipsed Michael Owen as the youngest goalscorer in Liverpool’s history to help seal a hard-fought victory for Jürgen Klopp’s side over Leeds United.

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Garry Monk’s Championship team pushed Liverpool close and created the better chances until Divock Origi punished hesitation by the goalkeeper, Marco Silvestri, to score his second goal in four days but the quarter-final belonged to Liverpool’s English-born Welsh international. Woodburn struck in front of the Kop with nine minutes remaining to put the quarter-final beyond Leeds and Owen into second place on the list of Liverpool’s youngest goalscorers. Owen was aged 17 years and 143 days when he opened his account against Wimbledon in May 1997. Woodburn beat the record by 98 days and, just in case anyone is not feeling old enough, the watching Steven Gerrard made his Liverpool debut before the winger was born, 18 years ago to the day.

A small slice of history “made it much more enjoyable” according to Klopp but until Origi and Woodburn struck in the space of five minutes this had been a nervous, disconcerting night for a much-changed, injury-hit Liverpool side. In contrast to Klopp’s eight changes Monk made four to the Leeds team that beat Rotherham on Saturday and the benefits of a relatively settled side showed immediately. Leeds were quick in the tackle and unnerved Liverpool’s defence whenever they got forward in numbers.

“We asked them to play in a slightly different way tactically and they followed it to a tee,” the Leeds manager said. The only thing lacking was that we didn’t take one of our opportunities,” said Monk. “The only disappointment is that with more luck or composure in our finishing we might have had a better result.” Monk’s assessment was fair.

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After a period of silence for the 75 people who died in the plane crash in Colombia, including members of the Chapecoense football team, the game opened with an intensity befitting a cup quarter-final. Leeds posed the early threat, giving Liverpool’s three-man central midfield no time on the ball and looking for the first-time pass behind Lucas Leiva and Ragnar Klavan. The tactic almost produced an early lead when Stuart Dallas lofted a perfectly weighted chip over the Liverpool defence to Hadi Sacko. The striker, just onside, raced clear on goal but a combination of a slight touch from the recovering Alberto Moreno and a fine save from Simon Mignolet diverted Sacko’s low shot.

Mignolet also saved from Kemar Roofe before Liverpool created a meaningful attack. The hosts lacked their usual fluency in the final third, understandably given the changes and the absentees, but their threat increased as Trent Alexander-Arnold and Sadio Mané began to prosper down the right flank.

The young Liverpool midfielder Ovie Ejaria created his side’s first opening with a fine pass that picked out Georginio Wijnaldum’s run through a crowded Leeds defence. The Holland international steered his shot towards the top corner but Silvestri produced an excellent save on his return to the team in place of Rob Green. Liverpool’s best chance before the interval came from a rare lapse in the Leeds rearguard when Silvestri and Kyle Bartley left a backpass from Kalvin Phillips to each other. Emre Can nipped in to poke the ball beyond the Leeds keeper but just wide of the far post.

Leeds went close to breaking the deadlock when Roofe almost punished a mistake by Kevin Stewart in stunning style. In keeping with much of the tie Leeds were quicker to react when Stewart collected Alexander-Arnold’s pass outside his own penalty area and was instantly hassled off the ball by Phillips. It broke to Roofe who curled a first time shot over Mignolet and raised his arms in celebration, as did Monk, only to see it strike the inside of the far post and rebound to safety.

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Bartley headed wide from a Charlie Taylor corner and Roofe was denied again, this time by Mignolet, as the threat from Leeds intensified. But they were made to pay for the missed opportunities. Wijnaldum served Leeds notice when he struck the inside of a post after Mané sent him clear on the right of the box. With Liverpool’s next attack, the deadlock was broken. Silvestri was caught in two minds when Alexander-Arnold whipped a dangerous cross towards his near post and, with the keeper rooted to his line, Origi slid in behind Luke Ayling to convert at full stretch.

Liverpool’s second may have glossed over the margin of victory but Woodburn had no complaints. The teenager replaced Stewart with 23 minutes remaining and was given a moment to cherish when Origi and Wijnaldum combined inside the Leeds area to present him with a free shot from close range. The Wales youth international obliged with an emphatic finish into the roof of Silvestri’s net and the semi-finals beckoned once again for Liverpool.