When the transfer windows open it gives soccer fans the chance to dream that their team will sign a superstar who propels their club to success and riches.

And sometimes Premier League managers hit the jackpot with bargains who turn out to be pure class. Examples include Eric Cantona, Thierry Henry, Tim Cahill, even Cristiano Ronaldo, who was a relative snip when Manchester United bought him for £12 million (considering the sold him for £80 million a few years later).

All too often, however, things go horribly wrong, as potential world-beaters turn into expensive flops who spend a season or two warming the bench (or the physio’s couch) before making a quiet exit for a fraction of the initial fee.

So read on for our pick of the ten worst signings in English Premier League history.

1. Alberto Aquilani – Roma to Liverpool, £17 million

Not the bargain of the century: a transfer fee of nearly £20 million along with wages of around £5 million a year and in return Liverpool got just 28 games and a miserly two goals from the Italian.

He was transferred to Fiorentina in 2012 for an ‘undisclosed fee’ which is sure to have been a fraction of what he cost the Reds. Goals can be priceless, but at nearly £10 million a pop, you wouldn’t fill your boots.

2. Adrian Mutu – Parma to Chelsea, £15.8 million

When Mutu started his Chelsea career with four goals in three games, all seemed rosy. But then the goals dried up, and so did his luck as the Romanian tested positive for cocaine in 2004.

The club sacked him a month later and are still trying to regain some of their losses for his breach of contract. It might end up in the European Court of Justice, which makes you wonder how many millions Chelsea have paid out in legal fees. All in all,
something of a disaster.

3. Andrei Shevchenko – AC Milan to Chelsea, £30 million

When you are a billionaire who owns a football club, you can pretty much sign who you want. Which is exactly what happened when Roman Abramovich encouraged his club to sign Ukrainian legend Shevchenko for a cool £30 million. This was despite the striker approaching his 30th birthday.

Despite the confidence shown in him by the club’s owner, Sheva was unable to repay the faith, netting just nine goals in 48 appearances. Considering he scored 127 times in 208 matches for Milan, this was more than disappointing for Chelsea fans. At £3.3 million per goal, not quite as bad as Aquilani, but certainly one of the biggest flops in Premier league history.

4. Winston Bogarde – Barcelona to Chelsea, Free

Another Chelsea flop (sorry Blues fans, it’s the last one, I promise!). How can a free transfer be a bad transfer, I hear you ask? Well, when that transfer is to purchase the services of one Winston Bogarde.

Early on in his Chelsea career the club made it clear Bogarde was surplus to requirements after they realized he wasn’t really very good. But someone had signed him on a four-year deal worth £40,000 per week. And the Dutch defender decided he wasn’t going anywhere. He managed just 11 games in four years, and Bogarde seemed happy enough collecting his pay cheque each week without the need to break a sweat or do what he was actually being paid for.

When ridiculed by the press for his cut-throat attitude he hit back saying, “This world is about money, so when you are offered those millions you take them. Few people will ever earn so many. I am one of the few fortunate’s who do. I may be one of the worst buys in the history of the Premiership, but I don’t care.”

It’s safe to say Chelsea fans cared.

5. Michael Owen – Real Madrid to Newcastle, £16 million

Many thought it was a strange choice by Michael Owen to join Newcastle after returning from his Spanish jaunt. Things started reasonably well though, until injury after injury plagued the striker.

Previously reliant on his turn of pace to steal a march on defenders, when he did play he rarely had the sharpness of previous years. In the end he managed just 71 games in four years before refusing a new contract and leaving on a free transfer to sit on Manchester United’s bench for a few years.

He’s now at Stoke City (probably injured).

6. Francis Jeffers – Everton to Arsenal, £8 million

Arsene Wenger is renowned for signing quality players for peanuts and selling them on for a huge profit. But even masters can make mistakes with their art. And Francis Jeffers was surely a mistake.

His three-year Arsenal career was intermittent at best due to a string of injuries. He scored four goals and apparently lost all confidence, gradually slipping down the leagues and last heard of playing for a Maltese Premier League side.

7. Steve Marlet – Lyon to Fulham, £11.5 million

Fulham are not known as the biggest spenders of the Premier League, so eyebrows were raised when the splashed a small fortune on this French striker.

After a return of just 11 goals from 54 matches, Fulham owner Mohammed Al Fayed accused the manager who signed the player (Jean Tigana) of deliberately paying over the odds in order to embezzle funds from the transfer.

Fayed lost the case in the High Court and Marlet was loaned out to Marseille before his contract with Fulham was cancelled. Not the ideal scenario for a club’s record signing.

8. Juan Sebastian Veron – Lazio to Manchester United, £28.1 million

He played 51 matches for Alex Ferguson’s team, and the vast majority of those performances erred more towards stale than style.

When Veron’s altogether mediocre play for United began to be pointed out in the press, Fergie had the audacity to tell a media gathering, “He is a f**king great player…And you’re all f**king idiots.”

Well, they weren’t the f**king idiots that signed him for nearly £30 million, Sir Alex.

9. Massimo Maccarone – Empoli to Middlesbrough, £8.15
million

Touted as a potential Italian great after impressing for his country at under-21 level, Maccarone was Middlesbrough’s record signing at the time. The club’s fans were brimming with excitement at this fantastic prospect, and the chairman, Steve Gibson, thought he’d landed a future star in what he saw as a transfer coup.

In reality Middlesbrough might have been as well spending the cash on £8 million worth of actual pasta given the paltry return of 18 goals in four years.

10. Ali Dia – Dijon to Southampton, Free

Football, the adage goes, is a funny old game. Never more so than when in 1996 the then Southampton manager Graeme Souness signed Ali Dia on a one month contract on the basis of a phone call. The man who called purported to be the one-time FIFA World Player of the Year, George Weah.

He said Dia was his cousin and that he was a real talent. Unfortunately for Souness and Saints fans, it was all blatant lies. In reality the caller was a university friend of Dia trying to help his buddy get a break in the Premier League.

Somehow the manager didn’t recognise Dia’s lack of ability on the training pitch and gave the lad a chance when bringing him on as a 32nd minute substitute against Leeds United. Sadly for Dia, he didn’t excel and played so badly he was hauled off the pitch after just 21 minutes.

Suffice to say he never played for Southampton again.

What do you think of the list? Did we leave anyone out? Let us know in the comments!