Gregory Vignal, Christian Ziege and Alberto Moreno also had their own respective struggles in the role.
Gerard Houllier came to an interim solution in the 2000/01 season when Jamie Carragher operated there for the campaign as Liverpool won three trophies.
And indeed, those were Jurgen Klopp’s problems finding the answer to the same equation 15 years later, he asked midfielder James Milner to play virtually the entire 2016/17 campaign there.
August 13 marks the Anfield debut of three more Liverpool left-backs who, for various reasons, also failed to cut mustard as a long-term option.
Andrea Dossena arrived from Udinese in the summer of 2008 to replace John Arne Riise and it was a gesture he was delighted to have made.
“Eighteen months ago, I never expected to play for one of the most famous clubs in the world,” he said.
“I don’t have any silverware in my collection in my career, but by signing for Liverpool I have a real chance to win medals in all the competitions we participate in.
Its debut came in an unremarkable – but ultimately important – 0-0 draw with an emerging side from Standard de Liège in qualifying for the Champions League in Belgium.
The game, played 12 years ago today, likely sums up Dossena’s time at Anfield in that few people remember the highlights.
The Italian claimed cult hero status for a week in March 2009 when he faced Real Madrid and Manchester United in famous wins for the Reds under Rafa Benitez, but for the most part, Dossena failed to justify the £ 8million spent on him.
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Which brings us to the left-back who prevented him from playing Fabio Aurelio.
Few would question the excellence of the elegant Brazilian on the left side of the defense, but getting him onto the pitch under optimal conditions was more than half the battle.
The day also marks Aurelio’s debut at Liverpool when the Benitez Reds saw Chelsea in the 2006 Community Shield. He combined superb technique with an underrated defensive us, but the fans just couldn’t. see it quite often.
Perhaps Aurelio, who joined Valencia on a free transfer, has become a better player as he has been on the treatment table.
In his two stays at Anfield – which from 2006 to 2012 – he made just 136 appearances and league games alone had 228 in that span.
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However, it is fondly remembered that the former Valencia player mainly prolonged Liverpool’s troubles due to his injury issues.
Jose Enrique was another whose Liverpool debut came on August 13, this time in a 1-1 draw at home against Sunderland on the opening day of the 2011/12 Premier League season.
The Spain full-back, who joined Newcastle for around £ 6million, was a reliable but unspectacular option for the Reds. Slowly but surely, however, his reputation began to wane at Anfield.
He played for Kenny Dalglish, Brendan Rodgers and Jurgen Klopp, but eventually left the club in May 2016 as his contract ran out in his final month.
The arrival of Andy Robertson just over a year later spelled the end of the Liverpool left-back’s long-term concerns.
After breaking into the squad with an injury to Moreno in December 2017, the Scotland captain has not looked back and has since become one of Europe’s best in the role.
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Klopp considers Robertson to be the best left-back in world football and the arrival of Kostas Tsimikas earlier this week has only strengthened a position that was a glaring weak point for so many years.
The Greece international will start the season as Robertson’s understudy, but he’s a player the club have been following closely for some time.
They believe he can provide some serious competition for Robertson in the next campaign and his £ 11.75million arrival from Olympiacos on Monday was the culmination of three years of scouting and surveillance in the hall recruiting club.
The left-back was not always the stronghold of Anfield but it is now a position of undoubted power.
This turbulent history could be about to get old.
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