The five-time champions of Europe have become synonymous with terrible transfers in recent years – Goal picks out their biggest flops

Liverpool are one of the most successful clubs in world football yet the five-time champions of Europe have not won the English title since 1990.

There are several reasons for their infamous league drought but there is no doubt that the Reds' often disastrous dealings in the transfer market have played a massive part.

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Indeed, whereas once Liverpool were renowned for shrewdly strengthening title-winning sides, now the Merseysiders are synonymous with flops and failures.

Below, Goal goes through the 15 worst signings that the Reds have ever made…

Getty ImagesPEGGUY ARPHEXAD | From Leicester | Free | 2000

The life of a reserve goalkeeper isn't easy. It's difficult to make an impact. However, even taking that into account, Pegguy Arphexad's time at Anfield was dreadfully underwhelming. Signed on a free transfer in 2000, on the back of one impressive outing against the Reds for Leicester, Arphexad managed just two Premier League appearances in three years on Merseyside.

His contribution was best summed up by Jamie Carragher's wonderfully sarcastic response to the news that his fellow pundit Gary Neville was quitting his job to take charge at Valencia.

"Gutted!" the former Reds centre-half tweeted. "This reminds me of when Pegguy Arphexad left for Coventry."

AdvertisementGetty ImagesIAGO ASPAS | From Celta | £7m | 2013

Iago Aspas reasons: "In football, you can’t live forever in the past." Unfortunately for him, though, his name has been written into Liverpool folklore for taking the worst corner in the club's history.

That shocking set-piece against Chelsea at Anfield – which saw him pass the ball straight to Willian while the Reds were pushing for a last-gasp equaliser that would have kept their Premier League title destiny in their own hands – will always be the Reds' fans abiding memory of the Spaniard.

It was his last ever touch in a Liverpool jersey, with Aspas – who failed to even net once in the Premier League – joining Sevilla on loan just months later before eventually returning to Celta.

Getty ImagesALBERTO AQUILANI | From Roma | £17m | 2009

In 2008, Rafael Benitez thought it would be a good idea to sell Xabi Alonso and replace him with Gareth Barry. It wasn't. But at least it didn't happen. However, Liverpool's horrified fans would have settled for Barry, given Alberto Aquilani turned up at Anfield the following year after Alonso had departed for Real Madrid.

The injury-prone Italian was plagued by injuries and made just 18 Premier League appearances before joining Fiorentina in 2012. "Maybe I should have stayed,” Aquilani later mused, “but I wanted to come back to Italy for family reasons."

Liverpool were happy to see him go, though, as underlined by the fact that they let him join Fiorentina for nothing.

Getty ImagesMARIO BALOTELLI | From AC Milan | £16m | 2014

No other deal better typifies Liverpool's incompetence in the transfer market than Mario Balotelli's move to Anfield in 2015.

Having reached the end of the transfer window without having acquired a world-class striker, manager Brendan Rodgers told captain Steven Gerrard at Melwood one day: "I'm basically left with no option but to have a bit of a gamble… The gamble is Mario Balotelli."

The captain's reaction? "Uh-oh."

Gerrard's concern was justified, with Balotelli scoring one Premier League goal for the Reds before being loaned to AC Milan and then sold to Nice.

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