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20 Worst Premier League Signings Of All Time

English Premier League is the most-watched football league in the world. Over the years, many great players have plied their trade in the league. Every year we see many great footballers showcasing their talent on the biggest stage. However, there had also been some poor signings in the competition’s history. In this article, we will have a look at some of the worst Premier League signings of all time.

Here are the 20 worst Premier League signings of all time.

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20. Ricky Van Wolfswinkel

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Van Wolfswinkel actually scored on his Norwich debut in 2013 which, at the time, seemed to indicate that the fine form he’d shown in the Eredivisie and the Primeira Liga could be reproduced in England. In fact, the £8.5m Dutch striker would never score another goal in 24 further Premier League matches.

Maybe the most obvious point to make about him concerned his body shape; he just didn’t look like a player suited to British football. Neat enough on the ball but frail and willowy, he had natural red flags which Norwich would have done well to recognize. Maybe there’s a case for saying that he might have been better in a superior side, or at least one built vaguely around his strengths, but that seems awfully generous.

19. Bebe

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One of the more baffling transfers in English football history, the arrival of Bebe at Manchester United for a reported £7.4m in 2010 was greeted with widespread confusion – especially when the normally meticulous Alex Ferguson admitted to having never seen him play. It arguably made more sense when it emerged that super-agent Jorge Mendes had just signed him as a client.

The Portuguese forward made seven appearances for United in his first season and generally equipped himself with the effort and lack of finesse of a competition winner. The remainder of his United career was spent out on loan, before he was sold to Benfica. He is definitely one of the worst Premier League signings of all time.

18. Michael Owen

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Still looked a quality signing in the beginning of his Newcastle career but unfortunately, an injury derailed him. His form never regained over four years, and injuries kept on creeping into his game.

He only managed 71 games in four years at the club and then left on a free transfer after refusing a new contract at the club. This upset everyone at the club considering how much they spent on bringing him there and the considerable amount he picked up in wages considering how much he had been injured and his lack of form over the years.

Checkout: Newcastle United Worst Ever Signings 

17. Roque Junior

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Brazilian defender Roque Junior played close to an hour of the 2003 Champions League final for AC Milan mere months before an ill-fated loan spell at doomed Leeds United, a union that lasted just one season.

Leeds conceded 25 goals in Roque Junior’s seven appearances for the club, including a 6-1 battering at the hands of newly promoted Portsmouth. He had earlier been sent off on his debut, and even a brace in the League Cup against Manchester United couldn’t save him. He is regarded as one of the worst Premier League signings of all time.

16. Roger Johnson

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When Wolves signed Johnson from relegated Birmingham, they were hoping to add a leader to their backline. The only place he led them was down the same path. With Johnson taking over as club captain, Wolves were immediately relegated.

The nadir of their season likely came when the defender was fined after showing up drunk for training in March, though there was further indignity when Wolves were relegated again the next year. Johnson never appeared for the club again.

Checkout: Wolves Worst Ever Signings

15. Milton Nunez

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An air of mystery still surrounds the arrival of diminutive Honduran striker Milton Nunez at Sunderland. Signed by Peter Reid for £1.6m on deadline day in 2000, Nunez made just one appearance for the Black Cats, and it’s been rumoured that Sunderland actually signed the wrong player.

Nunez had been playing for PAOK in Greece, alongside the (much taller) Colombia striker Adolfo Valencia, who legend has it is the person Reid was actually after. Nunez himself has given contradictory versions – in an interview 2016, he said he was absolutely the player Sunderland wanted to sign, but in 2017 he told a Honduran newspaper that the rumours were true. Nunez didn’t know what he was doing on Wearside, and no one else did either.

14. Marco Boogers

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Things started bad and didn’t get much better for Boogers, who was sent off in his second appearance for the Hammers after an attempt to saw off Gary Neville’s leg at the knee. Boogers would make just two more appearances for West Ham and finished his Premier League career with 100 total minutes on the pitch.

When he returned to the Netherlands during his four-game suspension for the Neville tackle, a misheard quote from West Ham’s press officer led the Sun to publish a headline suggesting Boogers had left the club to live in a Dutch caravan. The story wasn’t true, but, after a knee injury, he did return to his homeland to finish his career.

Checkout: Worst West Ham Signings Ever

13. Juan Sebastian Veron

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Veron was seen as the man to take Manchester United to the next level and make them perennial Champions League winners when they splashed out a record £28 million, but he just never seemed to adapt to English football. He was great on most of the big European occasions where he could have more time on the ball, but back in England, he never really adapted to the faster side of the game.

After his two disappointing seasons at United, Chelsea compounded United’s error by signing him for £15 million, and he carried on exactly where he left off. He did enough to earn himself a place among the worst Premier League signings of all time.

12. Andy Caroll

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Liverpool had already broken their transfer record on winter deadline day in 2011 to buy £23m Luis Suarez from Ajax, but smashed it to pieces mere hours later to land Newcastle striker Andy Carroll for £35m.

The Geordie target man had only 18 months of regular first-team football under his belt at that time and represented a huge panic buy for the Reds. Carroll scored four Premier League during his only full season and was eventually sold to West Ham in 2013 for a £20m loss.


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11. Fernando Torres

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The only reason Liverpool had £35m to spend on Andy Carroll in 2011 was because Chelsea had just given them £50m for Fernando Torres, an enormous figure that made him the third most expensive player of all time behind only Cristiano Ronaldo and Kaka.

The Spaniard had been an absolute revelation when he first joined Liverpool in 2008, but this was a player already on the wane while still at Anfield as injuries began to hit, affecting his electric pace and badly knocking his confidence.

That only worsened after moving to west London and Torres scored just 20 Premier League goals in three-and-a-half seasons at Chelsea. He is widely remembered as one of the worst Premier League signings of all time.

10. Tomas Brolin

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Brolin had suffered a serious foot injury on international duty for Sweden in 1994 and barely played for Parma before Leeds spent a club-record £4.5m to sign him in summer 1995.

Brolin actually wasn’t all that bad in his brief time playing with the club, scoring four goals in 18 Premier League appearances, including a brace in a 2-0 win over West Ham. With Leeds manager Howard Wilkinson choosing to play Brolin out of position, the Swede decided to respond with a deliberately awful performance in a 5-0 loss to Liverpool the next week. Brolin refused to return to Leeds the next season, went to Zurich to play on a minimum salary to prove his point about money not mattering, and then briefly went back to Parma on a loan.

With the striker alternately practicing with the reserves or skipping out on training altogether, Leeds eventually banned him from their stadium during matchdays before releasing him altogether. After a brief spell with Crystal Palace, Brolin retired from the game at 28.

Checkout: Worst Leeds United Signings Ever

9. Winston Bogarde

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Winston Bogarde’s four-year spell at Chelsea is infamous because the Dutchman, who had previously won the Champions League with Ajax and played for Barcelona, spent most of his time at the club simply training and collecting lucrative wages, without actually playing.

Claudio Ranieri had been hired shortly after Bogarde’s arrival and didn’t want him. But the defender had signed a contract worth €15m over four years and didn’t believe he could earn as good a salary anywhere else. So he stuck around until 2004 to take every penny he was owed.

8. Jo

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Brazilian striker Jo arrived at Manchester City a few weeks before the Abu Dhabi takeover in 2008 and the £19m paid represented a huge new record, albeit one that would be smashed when Robinho joined for £32.5m later that summer.

It became apparent that there was no place for Jo after only a few months. He showed he had quality after five goals in 12 Premier League games for loan club Everton, but that deserted him the following season. Back at City, he proved just as useless as before. He is undoubtedly, one of the worst Premier League signings of all time.

7. Massimo Taibi

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Massimo Taibi, cruelly dubbed ‘The Blind Venetian’ after his disastrous spell in England, has long been a source of embarrassment for Manchester United fans. He was bought for £4.5m, a substantial fee for a goalkeeper, but was shipped off back to Italy after four games.

The former AC Milan stopper overcame an early flap on his debut against Liverpool to put in a Man of the Match performance. But he allowed a tame shot to squirm through his body in a 3-3 draw with Southampton and was utterly hopeless as United were hammered 5-0 by Chelsea.

6. Alexis Sanchez

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United’s worst signing of the Premier League era, has to be this transfer that was seen as a coup at the time. Sanchez appeared set to join Manchester City before United’s cross-town rivals balked at the Chilean star’s wage demands. United handed Sanchez a four-and-a-half-year deal reportedly worth £391,000-per-week with £75,000 appearance bonuses and a £1.1m annual bonus in the hopes of the 28-year-old serving as the focal point of their post-Zlatan Ibrahimovic attack.

Instead, Sanchez scored just three Premier League goals in one-and-a-half seasons. While he has dealt with injuries, the reality is that the once-exciting winger has looked like a shadow of his old self. A slowed Sanchez doesn’t fit in Ole Gunnar Solskjaer’s counter-attacking style of play, and an attempt to reduce the wage bill led United to loan him to Inter. The Red Devils are still paying Sanchez more than £200,000-per-week to play in Italy.

5. Andriy Shevchenko

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Long perused by Chelsea and more importantly Roman Abramovich, it felt like he was the missing piece in the puzzle of Chelsea’s quest to finally win the Champions League. So when they finally got their man for £30 million, the rest of Europe looked on to see just how good Chelsea would become now they had signed the best striker in Europe.

He had been scoring for fun at Milan, but seemed to age overnight after his move to Stamford Bridge. Injuries, inconsistency and the resurgent form of Drogba limited Shevchenko to just nine Premier League goals in 48 appearances.


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4. Danny Drinkwater

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It’s difficult to even remember now, but when Chelsea signed Drinkwater in summer 2017, he was still on the fringes of the England picture and a regular in midfield for Leicester. At the time, it seemed as if Chelsea might have signed him at the last moment after Ross Barkley turned down a move to Stamford Bridge — Barkley would later head to Chelsea during the subsequent winter transfer window — but, at the very least, they would have expected Drinkwater to be part of their midfield rotation, given he had been key to Leicester’s incredible title win a year earlier.

Things obviously didn’t plan out that way for the former Manchester United trainee. Drinkwater made 12 Premier League appearances in his debut season with Chelsea, but after Antonio Conte left, the midfielder was floating out of relevance. He was then loaned out to Burnley in 2019.

3. Savio Nsereko

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Forgotten by most given that his stay in the Premier League was so brief, West Ham fans probably wish they could forget about Savio Nsereko, bought in January 2009 for what was then a club-record fee of £9m.

Why the Hammers paid so much for an unknown 20-year-old with barely any first-team experience remains a mystery, but it was quickly obvious it was a mistake. The Ugandan-born German failed to settle and didn’t score a single goal before leaving a few months later. He is regarded as one of the worst Premier League signings of all time.

2. Bosko Balaban

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Aston Villa signed Balaban from Dinamo Zagreb in 2001 for £7m. While £7m does not seem like an extravagant sum in the context of today’s transfer values, consider that this was the 23rd-largest transfer in the summer of 2001 for a Premier League club.

Balaban might be one of the least impactful signings in Premier League history. It took him eight months before he could complete a full 90-minute match, and even that came in the reserves. The Croatian never started, playing just 138 scoreless minutes across eight appearances, and was loaned back to Dinamo after a disastrous first season. After he threatened to spend the remaining 30 months of his contract in the reserves, Villa settled a deal to end his time in the Midlands after two years.

Checkout: Worst Aston Villa Signings Ever

1. Ali Dia

Inevitably, the worst Premier League player of all time is Ali Dia. This story remains ridiculous, no matter how many times you hear it, and it is indicative of how some of the country’s biggest football clubs were still being run with the professionalism and rigour of your local Sunday League team, well into the Premier League era.

Back in 1996, the then Southampton manager Graeme Souness, received a phone call claiming to be from Liberian international and former FIFA World Player of the Year, George Weah.

Weah told Souness that Dia was his cousin, had played for Paris Saint-Germain in France and had played 13 times for his country. In reality, none of this was true, and the phone call was made by a fellow university student of Dia’s to Souness, suggesting that he should give Dia a chance with the Saints. Nonetheless, Souness was convinced and signed Dia on a one-month contract.

Dia made his debut a couple of weeks later against Leeds United coming on as a 32-minute substitute. His quality of performance was so bad that he was dragged off the field 21 minutes later. This Southampton legend only spent a weekend at the club then was never seen by them again.



A sports addict! @subhamchaurasia

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