Liverpool’s worst Premier League signings of all time

Liverpool have been blessed with a remarkable collection of world-class players over the years, but not every signing has gone according to plan.

Some arrived at Anfield with hefty price tags and huge expectations, while others were regarded as exciting talents who simply could not find their feet on Merseyside.

For every Mohamed Salah, Virgil van Dijk or Sadio Mane, there have been deals that left Liverpool wondering what might have been. Transfer success is never guaranteed, and even the biggest clubs can get their recruitment wrong.

Here, FootballWhispers counts down Liverpool's five worst signings of the Premier League era.

5) Stewart Downing

Back in 2011, when £100m transfers were still the stuff of fantasy rather than the norm, Liverpool were prepared to spend big to bring Stewart Downing to Anfield.

The winger had enjoyed two impressive seasons with Aston Villa, prompting the Reds to part with £20m for his signature. Unfortunately for Liverpool, it quickly became apparent that the move was not going to deliver the expected return.

Downing managed just two goals in 46 appearances during his first season, and remarkably, failed to register either a goal or an assist in the Premier League throughout the entire campaign.

Things improved only marginally in his second year, when the left-footed winger scored five goals across all competitions. Liverpool eventually cut their losses, selling him to West Ham United for just £5m and taking a sizeable financial hit on a transfer that never really got off the ground.

4) Lazar Markovic

Post Rafa Benitez era was arguably Liverpool's darkest phase in their history, and it was marked by poor recruitments, resulting in club's gradual decline.

One of such players was Lazar Markovic, who joined the Reds in the summer of 2014 for a fee of £20m from Benfica.

The Serbian was rated highly at that time, with Chelsea being linked with a move too, and it felt like Liverpool had hit a jackpot by luring him to Anfield.

What followed was a catastrophe. Markovic made only 19 Premier League appearances, and spent three more years in wilderness on loan spells elsewhere before joining Fulham permanently.

3) Alberto Aquilani

When Liverpool lost Xabi Alonso to Real Madrid in the summer of 2009, they turned to Alberto Aquilani in the hope that the Italian could fill the enormous void left in midfield.

The Reds paid £17m to bring him in from Roma, but the move quickly became one of the club's more disappointing pieces of business.

Aquilani arrived with a reputation for technical quality, but persistent injury problems made it difficult for him to build any momentum at Anfield. When he did get on the pitch, he struggled to adapt to the relentless pace and physical demands of the Premier League.

The Italian managed just 28 appearances for Liverpool, scoring two goals, falling well short of the expectations that accompanied his arrival.

Aquilani subsequently spent time on loan at Juventus and AC Milan before eventually returning to Serie A with Fiorentina, where he was far more comfortable. For Liverpool, however, the big investment never came close to producing the impact they had hoped for.

Want to know who Liverpool might sign this summer? Check out our Liverpool transfer targets page.

2) El Hadji Diouf

El Hadji Diouf is perhaps the perfect example of why clubs should think twice before splashing the cash on a player immediately after a spectacular international tournament.

The Senegalese forward was one of the breakout stars of the 2002 World Cup, and Liverpool were convinced that he could bring the same magic to Anfield. The Reds therefore paid around £10m for his signature, a considerable investment at the time.

Instead, Diouf's two-year spell proved hugely underwhelming. He scored just six goals in 80 appearances, while the 2003-04 campaign was particularly forgettable as he failed to find the net in the Premier League. His attitude also reportedly caused frustration within the dressing room, with senior players unhappy with his approach in training.

By the end of the campaign, Diouf had become an increasingly unpopular figure around the club and an exit quickly became inevitable.

What makes the transfer even more painful for Liverpool supporters is the fact that the club had reportedly passed up the opportunity to sign Nicolas Anelka in favour of the Senegal international.

1) Liverpool's worst Premier League signing of all time: Andy Carroll

The January 2011 transfer window was a seismic one for Liverpool. Fernando Torres, the club's beloved striker, departed for Chelsea, while Luis Suarez arrived from Ajax to immediately capture the imagination of the Anfield faithful. But Liverpool were not finished there.

Determined to make another statement, the Reds broke their transfer record to sign Andy Carroll from Newcastle United on deadline day for £35m, a staggering fee at the time.

The imposing striker had terrorised Premier League defences on Tyneside, but what looked like a statement signing soon became a classic case of a square peg in a round hole.

Carroll's physical presence was never in doubt, but his game simply failed to translate at Anfield. Across three seasons, he made just 58 appearances and scored 11 goals, while a loan spell at West Ham further underlined how far the move had fallen short of expectations.

For a club that had just lost Torres and welcomed Suarez, Carroll was supposed to become the focal point of a new Liverpool attack. Instead, his record-breaking price tag became the defining feature of a transfer that never worked — making him the unfortunate choice for Liverpool's worst Premier League signing.