Ranking the 50 Worst Premier League Signings of All Time | OneFootball

For every shrewd piece of business that sees a club get the next big star on a bargain, there’s a transfer that’s remembered for all the wrong reasons. Whether it’s down to ludicrous transfer fees, off-field controversies, or performances that simply didn’t match expectations, Premier League history is littered with expensive flops. Here’s a ranking of the 50 worst Premier League signings of all time, where dreams quickly turned into nightmares.

There are some notable mentions I have to get out of the way before this list begins, so let’s give a quick nod to Joey Barton, who brought more chaos than quality to QPR, Marco Boogers, whose bizarre West Ham stint became legendary for the wrong reasons, and Benjani, whose famous nap almost derailed his move to Manchester City. Honourable mentions also go to Danny Ward for his forgettable Leicester spell, for his ill-fated time at Arsenal, and José Bosingwa, who perfectly summed up QPR’s struggles during their turbulent Premier League seasons.

The 50 Worst Premier League Signings

50. Ross McCormack – Aston Villa – £12m

From Fulham → To Aston Villa

Ross McCormack’s £12m move to Aston Villa in 2016 came with high expectations, given his impressive goal-scoring record in the Championship. However, things went south quickly. His on-pitch performances were underwhelming, but it was off the pitch where things got bizarre. McCormack’s infamous excuse of a “gate malfunction” for missing training summed up his time at Villa—plagued by issues, lack of fitness, and minimal returns. He was eventually loaned out and released, making this a costly mistake for Villa.

49. Odysseas Vlachodimos – Newcastle United – £20m

From Nottingham Forest → To Newcastle United

Signed in 2024 for £20m, Odysseas Vlachodimos arrived at Newcastle as a third choice goalkeeper, despite commanding a hefty fee. Unfortunately, with Nick Pope firmly established as the club’s first-choice keeper, Martin Dubravka as backup, Vlachodimos found himself rarely warming the bench. Spending that much on a player who didn’t significantly improve the squad raised plenty of eyebrows, and many believe the move was a way for both Newcastle and Nottingham Forest to bypass PSR regulations.

48. Ricardo Jiménez – West Ham – Free

From Espanyol → To West Ham

Signed on a free in 2019 as backup to Łukasz Fabiański, Roberto Jiménez quickly became infamous during his short stint at West Ham. When Fabiański got injured, Roberto stepped in—and things went downhill fast. His tenure was marred by costly errors, including an unforgettable own goal where he punched the ball into his own net against Burnley.

In just 10 appearances, he conceded 21 goals and failed to inspire confidence in the defence. His poor form played a significant role in the team’s slump and contributed to the sacking of manager Manuel Pellegrini. By January 2020, West Ham had seen enough and loaned Roberto out to Deportivo Alavés, ending his disastrous Premier League stint. Despite costing nothing in transfer fees, Roberto’s performances made him one of West Ham’s most notorious signings.

47. Mario Balotelli – Liverpool – £16m

From AC Milan → To Liverpool

Liverpool’s £16m gamble on Mario Balotelli in 2014 was an unmitigated disaster. Known for his erratic behaviour and mercurial talent, Balotelli struggled to adapt to Brendan Rodgers’ system. He managed just one league goal in 16 appearances before being loaned out and ultimately sold for a loss. Balotelli’s time at Anfield is remembered more for his off-field antics than anything on the pitch. His most memorable act in a Liverpool shirt was swapping his own at half time with Pepe during a Champions League game against Real Madrid.

46. Jordon Ibe – Bournemouth – £15m

From Liverpool → To Bournemouth

Bournemouth broke their transfer record to sign Jordon Ibe in 2016, expecting big things from the Liverpool academy graduate. Unfortunately, Ibe never lived up to the hype, scoring just three goals in 92 appearances. His form and confidence deteriorated, and he left the club on a free transfer in 2020. At 29, when he should be in the prime of his career he is playing in the Isthmian LeagueSouth Central Division for Hayes & Yeading United. A far cry from the heights that many thought he could have reached when Bournemouth signed him.

45. Andy Carroll – Liverpool – £35m

From Newcastle United → To Liverpool

Liverpool splashed out £35m on Andy Carroll in January 2011, making him the most expensive British player at the time. Carroll’s physical style and aerial dominance suited Newcastle, but he struggled with injuries and Liverpool’s more technical approach. He scored just six league goals in 44 appearances before being offloaded to West Ham at a significant loss.

The transfer made Carroll the eighth overall most expensive footballer at the time, and also the most expensive British footballer at the time. Liverpool were in desperate need to replace Fernando Torres who had just left for £50m to Chelsea. They signed Andy Carroll and Luis Suarez in the same window, the cheaper of the duo ended up being the better deal.

44. Baba Rahman – Chelsea – £21.7m

From Augsburg → To Chelsea

Chelsea spent £21.7m on Baba Rahman in 2015, hoping to strengthen their left-back position. Despite a promising start, Rahman quickly fell out of favour under multiple managers. During his time at Chelsea he almost had as many loans away from the club as appearances for it. After just 23 appearances in 8 years, he was loaned out repeatedly and never made a real impact at Stamford Bridge. During his time at the club he was regularly injured and even contemplated retiring, but was convinced not to by Chelsea Doctor, Paco Biosca.

43. Jean Michaël Seri – Fulham – £25m

From Nice → To Fulham

Fulham fans were initially thrilled when the club splashed £25m on Seri in 2018, as the Ivorian had been linked with Barcelona just a year earlier. At the time of signing, Seri was considered a coup for the Lilywhites and seen as the club’s biggest ever signing. Jean-Michael Seri was at the time a player who was dubbed the next Xavi. However, Seri flopped massively,  so beneath everyone’s expectations that fans began turning against him en masse. His technical style that he was renowned for in France didn’t suit the pace and physicality of the Premier League. Fulham were relegated that season, and Seri became one of the many expensive signings that season they regretted.

42. Giovani Lo Celso – Tottenham – £42.2m

From Real Betis → To Tottenham

Giovani Lo Celso was signed permanently in 2020 after a promising loan spell, but injuries and inconsistency derailed his time at Spurs. He was signed to be the long term successor to Christian Eriksen, but despite flashes of quality, he couldn’t secure a regular place in the starting XI. He was eventually loaned out to Villarreal twice, before returning back to Spurs in 2024. After what was seen as somewhat of a renaissance at the club Tottenham parted ways as he re-joined Betis on a four-year contract through to 2028. He has become instrumental to Betis since joining, showing form he couldn’t dream of in the white of Tottenham.

41. Kalvin Phillips – Manchester City – £45m

From Leeds United → To Manchester City

Phillips was a key figure for Leeds and a standout for England during Euro 2020, which prompted Manchester City to fork out £45m for his services in 2022. However, Phillips barely featured making just six competitive starts for City since a £42million move from Elland Road in 2022. This was largely due to fitness concerns and competition in City’s midfield. With just a handful of appearances, it’s hard to justify the fee paid for him. After failing on loan at West Ham last season, he has once again gone out on loan to Ipswich Town, where he has been an important player in their challenge to stave off relegation.

40. Robinho – Manchester City – £32.5m

From Real Madrid → To Manchester City

Manchester City made a huge statement by signing Robinho on deadline day in 2008, shortly after their takeover by Sheikh Mansour. Despite flashes of brilliance, Robinho’s commitment was often questioned, and he failed to adapt to English football. He left City after two seasons, having fallen out with management. In his first season, he was an incredible signing and looked like he was the player to bring Manchester City into their new era. In his second season at the club he refused to play and forced a loan back to Brazil before leaving for AC Milan. Thus making this an expensive early misstep for the club’s new era.

39. Benjamin Mendy – Manchester City – £52m

From Monaco → To Manchester City

Mendy arrived in 2017 as one of the most expensive defenders in history, with a reputation for attacking flair and athleticism. However, persistent injuries limited his impact on the pitch, and then legal issues including a rape charge, of which he was acquitted, stopped him from playing football for two years. Off-field issues, including legal troubles, ended his City career prematurely, making this one of the most disappointing signings in recent memory.

38. Angel Di Maria – Manchester United – £59.7m

From Real Madrid → To Manchester United

Di Maria’s move to Manchester United in 2014 was one of the most exciting transfers of the post-Ferguson era. He started well, but things unravelled after a burglary at his home unsettled his family. His performances dipped, and he looked increasingly disinterested. He was sold to PSG after just one season, with fans left wondering what might have been. This would have been higher up the list had Man United not recouped the majority of their fee when selling the mercurial winger to PSG the following summer.

37. Davy Klaassen – Everton – £23.6m

From Ajax → To Everton

Klaassen joined Everton in 2017 after captaining Ajax to the Europa League final. However, he struggled with the physicality of the Premier League Klaassen as he never once completed a 90 minute game of Premier League football. Due to the fast paced nature of the Premier League he failed to replicate his Ajax form, only managing 3 starts in the Premier League while at Everton. He lasted just one season, scoring no goals in 16 league appearances before being sold at a loss.

36. Bebe – Manchester United – £7.4m

From Vitória de Guimarães → To Manchester United

Signed by Sir Alex Ferguson in 2010 after being recommended by Carlos Queiroz, Bebe’s transfer remains one of the most baffling in Premier League history. Having never seen him play, United paid £7.4m for the forward, who managed just two league appearances before being loaned out multiple times. He eventually left for a fraction of the price, becoming a symbol of transfer market failure. There are suggestions that the deal was done by Sir Alex Ferguson as a favour to Carlos Queiroz due to Nani being ruled out of the world cup. But that is a conspiracy that I will let you read elsewhere. Bebe though, has had a good career in the top flight, so there was obviously a raw talent there, but his ceiling was below what Man United were.

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35. Winston Bogarde – Chelsea – Free

From Barcelona → To Chelsea

Bogarde’s arrival at Chelsea in 2000 is remembered not for what he did on the pitch, but for what he didn’t. He played just nine games in four years while collecting a hefty wage. Despite Chelsea’s efforts to move him on, Bogarde famously said he wouldn’t leave because no other club would pay him as well—a classic case of a bad deal. Bogarde saw out his entire £40,000-per-week contract before leaving in 2004. What is worth remembering is that, this salary was before Abramovich took over the club.

34. Tiemoué Bakayoko – Chelsea – £40m

From Monaco → To Chelsea

Bakayoko was signed in 2017 after impressing during Monaco’s run to the Champions League semi-finals. However, his performances were erratic, and he never looked comfortable in the Premier League. After just one season, Chelsea sent him out on a series of loans, and he never returned to Stamford Bridge in any meaningful capacity. While at Chelsea he was seen as The £40 million flop they could get rid of, he did eventually leave. In 2023, Bakayoko joined Lorient on a free transfer until 2025, but also there, he cut short his spell to move to Greece.

33. Darwin Nunez – Liverpool – £85m

From Benfica → To Liverpool

Nunez’s £85m price tag created sky-high expectations when he joined Liverpool in 2022. While he has shown flashes of his potential, he’s also been guilty of poor finishing and rash decision-making. He hasn’t justified his enormous fee, and it is easy to compare him to Erling Haaland who joined in the same summer. It is more likely at this stage that Nunez leaves Liverpool than succeeds there. Under Arne Slot he has become second or third choice as striker behind both Cody Gapko and Diogo Jota.

32. Guido Carrillo – Southampton – £19m

From Monaco → To Southampton

Southampton broke their transfer record in 2018 to sign Guido Carrillo, hoping he could be the answer to their goal-scoring woes. Instead, Carrillo failed to find the net in 10 appearances. He was loaned out the following season and eventually sold at a huge loss. Aside from Ali Dia, Guido Carrillo is arguably the biggest flop in the history of Southampton Football Club, which speaks volumes on how poor of a signing he was.

31. Stéphane Guivarc’h – Newcastle United – £3.5m

From Auxerre → To Newcastle United

Despite winning the World Cup with France in 1998, Guivarc’h’s move to Newcastle was a disaster. He scored just one goal in four league games before being sold to Rangers after only a few months. His signing remains a cautionary tale about judging players solely on international success. Guivarc’h was sold to Rangers for £3.5m in November 1998, just months after arriving on Tyneside.

30. Afonso Alves – Middlesbrough – £12.7m

From Heerenveen → To Middlesbrough

Middlesbrough splashed £12.7m on Afonso Alves in 2008 after he scored an astonishing 45 goals in 39 games for Heerenveen. Unfortunately, the Brazilian struggled to replicate that form in the Premier League, managing just 10 league goals in 42 appearances. Boro were relegated the following season, with Alves only netting 4 goals in 31 games, being largely at fault due to Middlesbrough’s terrible season with the club only scoring 28 goals. Alves was quickly offloaded to Qatar for a big loss, making this one of the worst transfers in the club’s history.

29. Saido Berahino – Stoke City – £12m

From West Brom → To Stoke City

Berahino’s £12m move to Stoke in 2017 came after a promising spell at West Brom. However, he failed to find the net in his first 35 appearances for the club. Saido Berahino did not score a competitive goal from 27 February 2016 to 28 August 2018, a goal drought of 913 days. Fitness issues and disciplinary problems plagued his time at Stoke, and he eventually left with the final three years of his contract torn up. He left the Potters after just three goals in 51 league games.

28. Roberto Soldado – Tottenham Hotspur – £26m

From Valencia → To Tottenham Hotspur

Soldado arrived at Spurs in 2013 with a reputation as a prolific goal-scorer in La Liga. However, he never adapted to the physicality of English football, scoring just 7 goals in 52 Premier League appearances. Despite a few penalties and Europa League strikes, he was widely considered a flop and was sold back to Spain after two disappointing seasons. The one positive from his failure was that it allowed Harry Kane to start more games for Spurs, and that ended up alright.

27. Kepa Arrizabalaga – Chelsea – £71.6m

From Athletic Bilbao → To Chelsea

Still the world’s most expensive goalkeeper, Kepa’s £71.6m move in 2018 quickly became infamous. Though he started well, errors and erratic performances soon crept into his game. His refusal to be subbed off in the 2019 League Cup final was a low point. Despite some recent improvement, Kepa has never fully justified his fee, and Chelsea eventually signed Édouard Mendy to replace him. And then about 9 more goalkeepers since. Kepa has moved on loan to Real Madrid, and now to Bournemouth. He is still the most expensive goalkeeper ever, and that doesn’t seem like it is going to change anytime soon.

26. Donny van de Beek – Manchester United – £35m

From Ajax → To Manchester United

Van de Beek was signed in 2020 after excelling for Ajax in the Champions League. However, he struggled to find a role in United’s midfield under multiple managers. Limited game time, coupled with underwhelming performances when he did play, turned this into a £35m flop. He was signed as a 10, and was inferior in just about every metric to Bruno Fernandes. He lacked the engine to play in midfield, and while fans called for him to play as a defensive midfielder, he lacked the engine for that. In Man United’s speed tests he would regularly be one of the slowest outfield players in the squad alongside Nemanja Matic. A loan move to Everton didn’t help matters, and he left for Girona during summer 2024 for a paltry £500k.

25. Eliaquim Mangala – Manchester City – £42m

From Porto → To Manchester City

Mangala’s £42m move in 2014 was meant to shore up City’s defence, but he never lived up to his hefty price tag. Prone to errors and lapses in concentration, Mangala quickly lost his place in the starting XI. After multiple loan spells, he left on a free transfer in 2019, making him one of City’s biggest transfer mistakes. Man City spent so much money on defenders over the years due to getting their signings wrong, and in the season following they signed Nicolás Otamendi, while the following season they signed Aymeric Laporte. Admitting through signings, they had gotten it wrong with Mangala.

24. Nicolas Pepe – Arsenal – £72m

From Lille → To Arsenal

Arsenal shattered their transfer record to sign Nicolas Pepe in 2019, hoping he would add firepower to their attack. Despite occasional moments of brilliance, he struggled with consistency and decision-making. He was loaned out in 2022 after falling down the pecking order, and Arsenal’s £72m outlay remains one of their most expensive blunders. Some people look back on his stats now and suggest he wasn’t a bad signing, and those people are idiots.

23. Francis Jeffers – Arsenal – £10m

From Everton → To Arsenal

Before Wayne Rooney, Everton had another prodigy, Francis Jeffers. Dubbed the “fox in the box,” Jeffers was signed by Arsène Wenger in 2001 to add a poacher’s instinct to Arsenal’s attack. However, injuries and poor form limited him to just four league goals in three seasons. He was sold back to Everton for a fraction of the fee, and the move is still regarded as one of Wenger’s rare transfer misjudgements.

22. Savio Nsereko – West Ham United – £9m

From Brescia → To West Ham United

West Ham splashed £9m on Savio Nsereko in 2009, but he failed to score a single goal in 10 appearances. He was sold after just six months, and reports later emerged that his agent inflated his transfer fee for personal gain. Nsereko’s brief, disastrous spell makes him one of the strangest and worst signings in Premier League history. Nsereko’s career was no better, a calamity of errors and poor decisions, including faking his own kidnapping, and he is now working as a personal trainer in Germany.

21. Christian Benteke – Crystal Palace – £32m

From Liverpool → To Crystal Palace

Benteke’s £32m transfer in 2016 was meant to make him Palace’s main goal threat, and he initially delivered with a solid first season. However, a dramatic loss of form saw him score just six goals across the next three seasons. Though he stayed at the club for several years, his inconsistency made this an underwhelming investment for Palace. That being said, Benteke has since proven himself to be a better scorer than Luis Suarez and Lionel Messi, as he went on to win the Golden Boot award in the MLS in 2024.

20. Sebastien Haller – West Ham United – £45m

From Eintracht Frankfurt → To West Ham United

After scoring 20 goals in the Bundesliga, Haller was signed by West Ham in 2019 for a club-record £45m. The French striker struggled to adapt to the Premier League’s physicality and pace, managing just 10 league goals in 48 appearances. He was sold to Ajax at a significant loss, where he rediscovered his goal-scoring form—leaving West Ham fans wondering what could have been. Haller is one of a number of forward signings who have failed at West Ham, including Danny Ings, Simeone Zaza, Jordan Hugill, Albian Ajeti, Jonathan Calleri, Maxwel Cornet (he should probably be included on this list), Gianluca Scamacca, Andre Ayew, Enner Valencia, Andriy Yarmolenko, Andy Carroll, and many more. Maybe West Ham are the issue.

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19. Naby Keita – Liverpool – £54m

From RB Leipzig → To Liverpool

Keita was signed in 2018 as part of Liverpool’s midfield rebuild, costing £54m. Despite occasional flashes of brilliance, his time at Anfield was hampered by injuries and inconsistency. After five underwhelming seasons, he left on a free transfer in 2023, leaving fans disappointed with his lack of impact due to the massive fee. When he was fit, he looked a player, unfortunately he was never fit. After leaving Liverpool he went back to Germany to Werder Bremen.

At Bremen, it was clear that he was no longer the player he once was, and he fell out with the board and team after refusing to to travel on the team bus for an away game against Bayer Leverkusen. This left his coach Ole Werner with no option but to banish the midfielder and have him train with the Under-23 side. Keita was sent away on loan to Ferencváros after failing to find a permanent deal elsewhere.

18. Jadon Sancho – Manchester United – £73m

From Borussia Dortmund → To Manchester United

United paid a hefty £73m to sign Jadon Sancho in 2021, hoping he would bring creativity and goals. However, the England international has struggled with form, fitness, and confidence since arriving. With inconsistent performances and limited impact, Sancho remains under immense pressure to justify his price tag.

17. Kalidou Koulibaly – Chelsea – £33m

From Napoli → To Chelsea

Koulibaly arrived at Chelsea in 2022 as an experienced centre-back, but his performances were erratic and often poor. He was caught out of position and struggled with the Premier League’s pace, Koulibaly didn’t live up to the reputation he built in Serie A as one of the world’s elite centre backs. He was sold after just one season to Al-Hilal for a large loss, making this another costly defensive flop for Chelsea. Chelsea were happy to accept the loss on the fee due to his long contract, sudden decline and massive wages.

16. Lazar Marković – Liverpool – £20m

From Benfica → To Liverpool

Liverpool spent £20m on Marković in 2014, expecting him to be a dynamic winger for years to come. However, he failed to adapt to the league, struggled with end product, and was loaned out multiple times. He made just 34 appearances in all competitions before leaving on a free transfer in 2019.

15. Shkodran Mustafi – Arsenal – £35m

From Valencia → To Arsenal

Arsenal splashed £35m on Mustafi in 2016, hoping he would solidify their defence. Instead, he became known for his frequent mistakes and erratic decision-making. His poor performances made him a scapegoat during Arsenal’s struggles, and he left the club on a free in 2021. The German World Cup winner left for Schalke, and then moved to Levante soon after. He retired on 25 June 2024 to become the assistant coach of the German U17 national team, having not played senior football after leaving Levante in 2023.

14. Jack Rodwell – Sunderland – £10m

From Manchester City → To Sunderland

Sunderland spent £10m on Jack Rodwell in 2014, but his time on Wearside was nothing short of disastrous. Injury-prone and unmotivated, Rodwell became a symbol of the club’s financial woes. His refusal to terminate his contract while Sunderland battled relegation further soured his relationship with fans. He became a focal point of the Sunderland ‘Til I Die Documentary and was derided as a mercenary for not leaving his contract early.

Eventually he did leave the club, after his salary got reduced to £43,000 a year when the club played in League One. With Rodwell knowing he would never earn the money he earned at Sunderland ever again, he was well within his right to stay at the club and continue earning what he had been. But that didn’t stop him being one of the worst signings in Premier League history.

13. Fábio Silva – Wolves – £35m

From Porto → To Wolves

In 2020, Wolves spent £35m on 18-year-old Fábio Silva, giving him a five-year deal while also making him the club record signing. The young forward struggled with the step up in quality, managing just four goals in 54 league appearances. He is now on his fourth loan spell away from the club and turned 22 in the summer. While he still has time to develop, the price tag and immediate lack of return make this transfer one of the worst in Wolves’ history. Silva is under contract at Molineux until 2026, with the club holding the option of another year, but the whole deal reeks of something dodgy.

In fact, the transfer was investigated, Correio da Manha (A Portuguese newspaper), claimed the authorities want to know why Porto did not receive a larger proportion of the €40million fee Wolves paid. The Primeira Liga giants were due to keep roughly €30million (£25.6m) after paying commissions to agency GestiFute and STV – a company owned by Silva’s father – valued at €7million (£6.0m) and €3million (£2.6m) respectively. The fact that Wolves paid £40m for someone with barely any first team experience alone should have raised all the suspicions. Alas, nothing seemed to come from the investigation, nor did anything of Fábio Silva’s time at Wolves.

12. Paul Pogba – Manchester United – £89m

From Juventus → To Manchester United

Pogba’s £89m move in 2016 made him the world’s most expensive player at the time. The man had returned after leaving as a boy on a free transfer to Juventus. #Pogback, dabbing, it was a simpler time. Despite moments of brilliance, his six-year spell was overshadowed by inconsistency, injuries, documentaries, transfer requests and off-field drama. United failed to build a team around him, and it could be said that the club failed him.

But the same could be said of Pogba failing Man United. He left again on a free transfer in 2022 — and has once again gone back to Juventus. It hasn’t been as positive the second time round, with Pogba getting banned for drug offences, witchcraft accusations against French national teammates, and his brother kidnapping him. Man United haven’t made a lot of good deals in the transfer market over the last 10 years, but not giving Pogba the monster contract he wanted to stay was undoubtedly one of the best.

11. Alexis Sanchez – Manchester United – Swap Deal

From Arsenal→ To Manchester United

Alexis Sánchez’s move from Arsenal to Manchester United in January 2018 was one of the most high-profile transfers in Premier League history. United secured the Chilean forward in a swap deal involving Henrikh Mkhitaryan, offering Sánchez a staggering wage package reportedly worth £500,000 per week. Expectations were sky-high, given his stellar record at Arsenal, where he had been one of the league’s most dynamic attackers.

However, Sánchez never came close to replicating his Arsenal form at Old Trafford. He managed just three league goals in 32 appearances, often looking a shadow of his former self. His confidence appeared shattered, and injuries further hampered his impact. Despite several chances under both José Mourinho and Ole Gunnar Solskjær, Sánchez failed to justify his enormous salary.

By 2019, United were desperate to cut ties. He was loaned to Inter Milan before being sold permanently, with United reportedly continuing to pay a portion of his wages during his loan spell.

10. Jack Grealish – Manchester City – £100m

From Aston Villa → To Manchester City

City made Grealish the most expensive British player in history in 2021, expecting him to be a game-changer. While he contributed to City’s title-winning campaign, his performances have been inconsistent, with many questioning whether he’s worth the £100m fee. When signing for City, Grealish was an exciting, flamboyant creator who has the skill of Gascoigne and the dribbling too. While at Villa he had a free role and he was given the chance to be the creator, at City he had to re-learn football. Grealish has yet to become the star City hoped for, and is a shadow of the player he once was. Grealish’s time as City will be more remembered for his celebrations during their treble season than anything he has ever done on the pitch.

9. Tanguy Ndombele – Tottenham Hotspur – £63m

From Lyon → To Tottenham Hotspur

Signed in 2019 for a then-club record fee, Ndombele showed glimpses of his talent but never found consistency. His work rate and fitness were repeatedly criticised by managers, and he was loaned out multiple times. Despite the massive outlay, Spurs failed to get the best out of him, making Ndombele one of their worst-ever signings. Ndombele’s failings seemed to be caused all by himself, too. He had all the ability in the world, but his attitude was what separated him from becoming world class. He was Tottenham’s highest earner alongside Harry Kane at one point, since then he has been released and signed for Nice in Ligue 1.

8. Rhian Brewster – Sheffield United – £23.5m

From Liverpool → To Sheffield United

Sheffield United splashed £23.5m on Brewster in 2020, hoping he would fire them to safety. Instead, the young forward failed to score a single league goal in his first season, as the Blades were relegated. Even in the Championship, Brewster hasn’t found his form, turning this transfer into a nightmare for United. In 95 games for Sheffield United he has scored 6 goals. People talk about potential, and seeing a player in there, but at 24 years old, it seems that the potential was just that, and it seems to be left unfulfilled.

7. Fernando Torres – Chelsea – £50m

From Liverpool → To Chelsea

Chelsea broke the British transfer record in 2011 to sign Torres, who had been prolific at Liverpool. However, everyone could see that Chelsea were getting a player who had been ruined by injuries and a loss of confidence. These issues plagued his time at Stamford Bridge. Despite a memorable goal in the Champions League semi-final against Barcelona, Torres managed only 20 league goals in 110 appearances, making this a hugely disappointing deal. Torres’ spell at Chelsea would be summed up by his open goal miss against Man United, where he rounded the keeper and still didn’t manage to put the ball in the empty net.

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6. Ali Dia – Southampton – Free

From Nowhere → To Southampton

Ali Dia’s story is legendary. He tricked Southampton manager Graeme Souness into thinking he was George Weah’s cousin, earning a one-month contract without much of a trial. His only Premier League appearance lasted just 53 minutes before he was subbed off due to an abysmal display. Despite costing nothing in transfer fees, the sheer absurdity of this deal makes Ali Dia one of the worst signings ever. The only reason he isn’t first is because he didn’t cost a fee, and it was only for 53 minutes. If anything, its more comical than bad.

5. Adrián Mutu – Chelsea – £15.8m

From Parma → To Chelsea

Adrián Mutu’s move to Chelsea in 2003 had all the makings of a success story. The Romanian forward was coming off a stellar season at Parma, where he scored 18 goals in Serie A. Signed for £15.8m during Roman Abramovich’s first summer of spending, Mutu was part of an exciting new era at Stamford Bridge. He made an immediate impact, scoring four goals in his first three games and quickly becoming a fan favourite.

However, Mutu’s bright start didn’t last. His form dipped during the second half of the season, and rumours began to surface about problems off the pitch. When José Mourinho replaced Claudio Ranieri as Chelsea’s manager in 2004, Mutu found himself on the fringes. His relationship with Mourinho soured quickly, culminating in a public falling out.

The situation reached a breaking point in October 2004 when Mutu tested positive for cocaine. Chelsea terminated his contract immediately, citing gross misconduct. To make matters worse, FIFA ordered Mutu to pay Chelsea £14.6m in damages, an amount that led to years of legal wrangling. Mutu later admitted he turned to drugs due to personal struggles and the pressure of living up to expectations.

For Chelsea, Mutu’s signing represented a significant financial and reputational loss. He played just 27 games and scored 10 goals for the club, a meagre return on a substantial investment. Despite his talent, his off-field issues overshadowed everything he did on the pitch, making him one of the Premier League’s most infamous signings.

Even after leaving Chelsea, the saga continued. Mutu rebuilt his career in Italy, thriving at Fiorentina, but the damage to Chelsea was already done. The legal battles over the damages dragged on for over a decade, cementing Mutu’s place among the worst signings in the club’s history.

4. Jean-Kévin Augustin – Leeds United – £18.4m

From RB Leipzig → To Leeds United

Leeds United’s signing of Jean-Kévin Augustin in January 2020 seemed like a bold move at the time. The French striker, once a hot prospect at Paris Saint-Germain and RB Leipzig, had fallen out of favour in Germany but was still seen as a player with untapped potential. Leeds, fighting for promotion to the Premier League under Marcelo Bielsa, brought him in on a loan deal with an obligation to buy if they secured promotion.

However, the move turned into a nightmare almost immediately. Augustin struggled with fitness from the outset and played just 48 minutes across three substitute appearances. Bielsa’s demanding style and intense training regime appeared to be too much for a player who hadn’t played regularly in months. With recurring muscle injuries, Augustin never got up to speed, and Leeds ultimately chose not to retain him once their promotion was sealed.

The real disaster came after Augustin left. Due to a contractual clause, Leeds were legally bound to pay RB Leipzig £18.4m, even though the player never featured for them in the Premier League. Leeds contested the payment, claiming the obligation was void because the season was extended due to the COVID-19 pandemic. After a lengthy legal battle, FIFA ruled in Leipzig’s favour, forcing Leeds to pay the fee for a player who contributed next to nothing.

In the end, Augustin’s time at Leeds became one of the strangest and most costly sagas in recent football history. Despite barely kicking a ball, he ended up costing the club millions, making this one of the worst deals not just in Premier League history, but football history.

3. Antony – Manchester United – £85m

From Ajax → To Manchester United

When Manchester United signed Antony in the summer of 2022 for £85m, it marked the second-highest transfer fee in the club’s history. The Brazilian winger was brought in by Erik ten Hag, who had coached him at Ajax, with hopes that he would bring flair, creativity, and goals to United’s attack. However, Antony’s time at Old Trafford has been marked more by inconsistency and frustration than brilliance.

The massive fee raised expectations that Antony has struggled to meet. While he’s shown flashes of his technical ability and scored some spectacular goals, his overall output has been underwhelming. Critics have also pointed out his predictable style of play. Antony is heavily reliant on his left foot and often cuts inside, making him easier for defenders to neutralise. His decision-making in the final third has also been questioned, with numerous wasted opportunities and misplaced passes. Additionally, Antony’s showboating—such as spinning tricks with no clear purpose—has drawn criticism, especially when it hasn’t been accompanied by effective end product.

Beyond his on-pitch struggles, Antony has faced controversy off the field. Allegations of misconduct have surfaced, creating further distractions and tarnishing his reputation. While these matters are still under investigation, they’ve added another layer of scrutiny to a player already under immense pressure to justify his price tag.

Antony still has time to improve and prove his doubters wrong. However, for now, his transfer fee looms large, and his performances haven’t come close to justifying United’s eye-watering investment and he barely gets minutes on the pitch to turn it around. With a move away from Man United looking likely after Ruben Amorim has replaced Erik ten Hag, the likelihood is that he will not be able to justify the fee paid for him.

2. Romelu Lukaku – Chelsea – £97.5m

From Inter Milan → To Chelsea

Romelu Lukaku’s £97.5m return to Chelsea in the summer of 2021 was meant to be the fairytale comeback of a striker who had matured into one of Europe’s best. After leading Inter Milan to a Serie A title with 64 goals in 95 appearances, Chelsea believed Lukaku would solve their long-standing issues up front. Instead, it turned into one of the costliest disasters in Premier League history.

Lukaku started his second spell brightly, scoring four goals in his first four games, but things quickly went south. Struggling to fit into Thomas Tuchel’s system, he often appeared isolated, ineffective, and uncomfortable with the tactical demands placed on him. His infamous struggles with his first touch returned, making him a liability in possession. Despite being signed to provide a consistent goal-scoring threat, he managed just eight league goals in 26 appearances, far below expectations for a player of his calibre.

Off-field controversy further derailed Lukaku’s time at Chelsea. In December 2021, he gave an unauthorised interview to Sky Italia in which he criticised Tuchel’s tactics and expressed a desire to return to Inter Milan. This bombshell caused a major fallout between Lukaku, Tuchel, and the club’s hierarchy, leading to his temporary exclusion from the squad. Though he apologised, the damage was done—both his relationship with the fans and his confidence on the pitch were shattered.

By the end of the 2021/22 season, Chelsea were desperate to move him on. Lukaku was loaned back to Inter Milan in the summer of 2022, just a year after his record-breaking arrival. However, Inter didn’t pursue a permanent transfer, and in 2023, Chelsea loaned him out once again—this time to Roma. After multiple underwhelming loan spells and mounting wage costs, Chelsea finally managed to sell Lukaku in the summer of 2024 to Napoli for €30m, representing a staggering financial loss on their original investment.

Lukaku’s second stint at Chelsea stands as a prime example of poor planning, inflated fees, and a complete breakdown in player-club relations. What began as a marquee signing ended in disappointment, off-field drama, and a massive financial hit for Chelsea, cementing Lukaku’s place as one of the worst Premier League signings of all time.

1. Mykhailo Mudryk – Chelsea – £88.5m

From Shakhtar Donetsk → To Chelsea

Chelsea’s acquisition of Mykhailo Mudryk in January 2023 for £88.5 million was a significant statement of intent. The Ukrainian winger was expected to inject pace and creativity into the squad. At Shakhtar his stock had risen so much due to Champions League displays, that Arsenal, Brentford and Chelsea were all linked. With Chelsea eventually winning his signature. He signed an 8 year deal on large wages so that the club could amortise his wages over the course of his contract. However, his tenure at Stamford Bridge has been fraught with challenges both on the field, and off it.

Initially, Mudryk struggled to adapt to the Premier League’s intensity, managing only a handful of assists and failing to score in his first season. Critics pointed to his lack of physicality and decision-making as key factors in his underwhelming performances. Despite flashes of his potential, consistency remained elusive. His pace would get him into positions, but then he would fluff chances or make poor decisions when he got into the more advanced spots.

The situation worsened in December 2024 when Mudryk was provisionally suspended after testing positive for meldonium, a banned substance. The test, conducted in October, revealed the presence of the drug in his system. Mudryk has denied knowingly ingesting any prohibited substances and is cooperating with authorities to determine the cause of the adverse result.

If the B-sample confirms the initial findings, Mudryk could face a ban of up to four years, effectively sidelining him during his prime playing years. This development not only jeopardises his career but also represents a significant financial and reputational blow to Chelsea. The club, already under scrutiny for its transfer expenditures, may have to reassess its investment strategies and player support systems.

In light of these events, Mudryk’s transfer has to be viewed as the most ill-fated in Premier League history. The combination of a hefty transfer fee, lacklustre performances, 8 year contract and potential long-term suspension all tallies up to the worst signing in Premier League history.