Liverpool are looking to the January transfer window for a solution to their stuttering season, with the Reds embroiled in a battle to finish in the top four.
Jurgen Klopp's side have endured a disappointing start to the campaign, with midfield in particular proving to be a major issue. If Klopp does look to the market to fix the problems his team is having in that position, he will do well to look back at past transfer mistakes.
Some of those errors have been committed while the German has been in charge, though even before Klopp arrived the Reds had made mistakes in January. Here, Mirror Football looks at seven of the worst mistakes Liverpool have made in the winter window.
Ozan Kabak (January 2021)
Liverpool reportedly paid £1million to bring highly-rated defender Ozan Kabak to Anfield in January 2021. The Reds were experiencing an injury crisis at centre-back, with Kabak brought in to help relieve that.
But he endured a disastrous debut at Leicester, leading to Klopp's men suffering a 3-1 defeat at the King Power. He would make just nine Premier League appearances in total, losing his place in the team to youngsters Nat Phillips and Rhys Williams.
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Ben Davies (January 2021)
Like Kabak, Ben Davies was also brought to Liverpool to help relieve the defensive injury crisis that hit the Reds during the 2020/2021 campaign. Davies had impressed at Preston North End, but he failed to make an appearance that season.
He was then sent on loan to Sheffied United the following campaign, with Klopp not seeing a place for him in his plans. The Englishman was sold to Rangers last July for an inital £3m, where he has been a regular.
Mauricio Pellegrino (January 2005)
Mauricio Pellegrino arrived at Anfield with a big reputation from his time at Barcelona and Valencia in Spain, winning La Liga three times. He joined Liverpool in January 2005, but failed to live up to his reputation.
He endured a dreadful debut against Southampton and would make just 13 appearances in total before being released at the end of the season. Worst of all, he was cup-tied for the Champons League, meaning he did not pick up a winner's medal following the famous win over AC Milan in Istanbul.
Marko Grujic (January 2016)
Bringing in Marko Grujic was something of a coup for Klopp, with Liverpool beating the likes of Barcelona, Real Madrid and Chelsea to his signature. Klopp was personally involved in bringing him to Anfield, but did not appear to have a plan for how to use him.
Instead, he was sent out on a series of loans, to Cardiff City, Hertha Berlin and Porto. After making only 16 appearances in five years for Liverpool, he joined Porto permanently last summer.
Jan Kromkamp (January 2006)
Having struggled for game time at Villareal, Jan Kromkamp joined Liverpool in January 2006. The right-back made his debut in the win over Luton Town in the FA Cup that month, but failed to break past first-choice Steve Finnan.
Most of his appearances came from the bench, with a lack of pace meaning he was never considered a first-choice option. In August 2006, he was on his way out of Anfield, joining PSV Eindhoven.
Steven Caulker (January 2016)
Signed on loan from Queen's Park Rangers in January, Steven Caulker had been a solid centre-back for lower table teams. He only played three times for Liverpool in the Premier League though.
Bizarrely all three of those appearances came as an emergency striker late into matches. He was sent back to QPR at the end of the season, with his move to Anfield having been somewhat of a waste of time.
Andy Carroll (January 2011)
Perhaps the most infamous of Liverpool's January transfer mistakes was the decision to sign Andy Carroll. The Reds made him the then-most expensive British player of all time by paying Newcastle £35m for him.
He struggled for injuries and form though, scoring just six Premier League goals before being sent to West Ham on loan in 2012. That deal was made permanent a year later, with Liverpool taking a £20m loss to send him to the Hammers.
