The 50 least successful transfers in Premier League history
When a series of transfers goes well, it can transform everything. Many of the successful runs in the Premier League era were constructed on such foundations, and, as expected, some of the most remarkable teams in league history have been formed through exceptional transfers.
Conversely, the wealthiest clubs in the Premier League have occasionally managed to navigate through poor transfer decisions. Chelsea still clinched the Champions League in 2021 despite several missteps, and Manchester City continued to secure numerous league titles even after not fully capitalizing on investments like Kalvin Phillips. Nevertheless, these issues typically catch up with teams over time.
There are numerous ways a transfer can go awry.
Perhaps a player’s injury history was overlooked, leading to negative consequences. Maybe a player’s injury issues began only after he made a high-profile move to your club. You might also dismiss the manager who advocated for his signing, resulting in the player never feeling settled. (Additionally, if his contract is substantial enough, he may be content to remain on the bench despite your attempts to offload him.) Conflicts with teammates can arise, or a player might be signed just past his prime. Alternatively, you might have negotiated poorly and significantly overpaid.
– Connelly: The best 50 transfers in Premier League history
– O’Hanlon: Ranking club, national team coaching jobs from best to worst
– Lindop: Where did it go wrong for Arne Slot and Liverpool?
Regardless of the cause, some disastrous transfers stand out prominently. As we proceed, you will notice recurring themes, but here are the 50 most regrettable transfers in Premier League history.
50. Davy Klaassen, CM, Everton
Signed from Ajax for €27 million, 2017-18
A notably disappointing transaction. Klaassen joined as a highly regarded 24-year-old midfielder, having captained Ajax for the previous two seasons, and was seen as a vital addition for manager Ronald Koeman, also from the Netherlands. However, just one year and 251 Premier League minutes later, he departed for Werder Bremen at half the original fee. He could not prevent Koeman’s dismissal and failed to impress either Sam Allardyce or Marco Silva the following summer.
49. Casemiro, DM, Manchester United
Signed from Real Madrid for €70.7 million, 2022-23
There is enough content to compile a substantial “Worst Premier League transfers of 2022-23” list. Five players from those two transfer windows made this list, alongside four more from 2021-22. To be fair to Casemiro, he initially appeared to justify the investment. (He was not even the worst signing United made that season.)
The Brazilian provided valuable veteran leadership, contributing seven goals and six assists for a United team that improved from sixth to third in the Premier League, won the League Cup, and reached the FA Cup final. However, that was three years ago, and the challenge with signing a 30-year-old for a significant fee is that he will only age further. While earning a yearly salary around €20 million, Casemiro’s output declined sharply over the next two seasons as United fell to eighth and then 15th.
He has shown some improvement recently, but he has struggled to justify his salary.
48. Gastón Ramírez, AM, Southampton
Signed from Bologna for €15.2 million, 2012-13
After two consecutive promotions that returned them to the Premier League, Southampton enjoyed a successful run in the top division during the 2010s, but Ramírez contributed very little to that success. After scoring eight goals and providing four assists in league play for Bologna in 2011-12, he was a standout among a group of young attackers Southampton brought in. However, over parts of four Premier League seasons with the Saints, he managed only six goals and seven assists. Following several loan spells, he left for second-tier Middlesbrough on a free transfer before eventually finding some success with Sampdoria. Some players only thrive in Italy.
47. Roberto Soldado, CF, Tottenham Hotspur
Signed from Valencia for €30 million, 2013-14
Similar to Klaassen, Soldado departed at a 50 percent discount shortly after his arrival. A record signing for Spurs following a 30-goal season at Valencia, he netted three goals in his first week at the club—one against Crystal Palace in the Premier League and two against Dinamo Tbilisi in the Europa League—but it was downhill from there. He added five more goals in 14 Europa League matches but managed only seven goals in 29 Premier League starts over two seasons. He transferred to Villarreal for €16 million in 2015.
46. Alberto Aquilani, MF, Liverpool
Signed from Roma for €20 million, 2009-10
After five successful seasons with Roma, Aquilani departed due to the club’s financial difficulties, and although he was seen as a successor to Xabi Alonso, he fell short of that expectation. He started only nine league matches for Rafa Benitez’s Liverpool and, despite providing six league assists, the transfer was quickly recognized as a misstep by all involved. He was loaned to Juventus for one season and to AC Milan for another before moving to Fiorentina for just €2 million in 2012.
45. Owen Hargreaves, DM, Manchester United
Signed from Bayern Munich for €25 million, 2007-08
It is challenging to evaluate a transfer negatively when injuries significantly impact a player’s performance, but with Hargreaves, there were clear warning signs: he had only surpassed 1,700 league minutes once in his previous five seasons with Bayern. He excelled in his first season at Old Trafford, playing all 120 minutes in United’s Champions League final victory over Chelsea. However, recurring knee problems plagued him afterward, and he made only five more appearances for the club following the 2007-08 season.
44. Marco Boogers, CF, West Ham United
Signed from Sparta Rotterdam for €440,000, 1994-95
There are few signings from the 1990s on this list, as there was not as much money wasted proportionally during that time. However, Boogers deserves a spot on the list; in his second appearance, he committed one of the most notorious tackles in league history on Gary Neville, suffered a knee injury shortly after returning from suspension, and was sent back to the Netherlands by February 1998, never to be heard from again in England.
43. Timo Werner, FW, Chelsea
Signed from RB Leipzig for €53 million, 2020-21
This is a classic example of a “no-brainer that somehow didn’t pan out.” After transferring from Stuttgart at age 20, Werner was phenomenal for RB Leipzig, scoring 95 goals in four seasons across all competitions. He was incredibly fast in both pressing and counterattacking, and while his finishing was never top-tier, it was at least average.
He chose Chelsea over significant interest from Liverpool and others, but during his two seasons at Stamford Bridge, his finishing deserted him: he scored 23 goals from shots with an expected goals value of 34.0. He started in Chelsea’s Champions League final victory over Manchester City in 2021, and while 23 goals in two seasons isn’t poor, it also didn’t meet the expectations set by his résumé or transfer fee.
42. Seth Johnson, MF, Leeds United
Signed from Derby County for €11.5 million, 2001-02
Acquired following Leeds’ Champions League semifinal run, Johnson took advantage of the club’s urgency to remain competitive and received a significant pay increase. Leeds found themselves burdened with his contract when they faced financial collapse and were relegated a few years later. Johnson was not ineffective, but he struggled with persistent injuries and made only 15 Premier League starts in his first two seasons. As the narrative goes, he returned to Derby after leaving Leeds, where he was quite impressed by the facilities that his transfer had enabled the club to develop.
41. Michael Owen, FW, Newcastle United
Signed from Real Madrid for €25 million, 2005-06
At just 25 years old after a lengthy, successful tenure at Liverpool—and a much shorter, less fruitful period at Real Madrid—Owen arrived at St. James’ Park as Newcastle’s record signing and intended replacement for the retiring Alan Shearer. (There are numerous record signings on this list.) Initially hindered by an injury, he still managed to score seven goals in his first eight Premier League matches with the club. However, he broke his foot on New Year’s Eve and missed most of the next four months, followed by an ACL tear at the 2006 World Cup that sidelined him for most of the 2006-07 season. He rebounded for a couple of decent seasons, but “30 goals and 79 total appearances in four years” did not meet Newcastle’s expectations.
40. Fernando Torres, FW, Chelsea
Signed from Liverpool for €58.5 million, 2010-11
Chelsea effectively paid €58.5 million for this:
Fernando Torres vs Barcelona 🔵
Iconic.#UCL pic.twitter.com/Ma2z6kCTXt
— UEFA Champions League (@ChampionsLeague) November 25, 2025
However, that moment might have justified the cost. Roman Abramovich’s Blues secured a long-awaited Champions League title when Torres scored to defeat Barcelona in the semifinals, and Chelsea triumphed over Bayern on penalties in the final. Yet, as the most expensive Premier League transfer at that time, Torres primarily made an impact in continental competitions. In 3½ seasons, he scored nearly as many goals in UEFA competitions (17) as he did in Premier League matches (20).
39. Sergey Rebrov, FW, Tottenham
Signed from Dynamo Kyiv (Ukraine) for €18 million, 2000-01
Including qualification matches, Rebrov netted 31 goals with 12 assists in the Champions League during a career that spanned nearly two decades. Unfortunately, none of those came while at Tottenham. Acquired after a stellar 30-goal season with Dynamo Kyiv (his second in three years), Rebrov managed just 15 goals in all competitions over two seasons in North London and was loaned out for two unproductive seasons with Fenerbahce. He departed as a free transfer four years after his arrival.
38. Per Kroldrup, DF, Everton
Signed from Udinese for €6.8 million, 2005-06
Blink and you might have missed Kroldrup’s time at Everton. The 6-foot-4 Dane arrived after playing a significant role in Udinese’s impressive rise, but he quickly suffered a groin injury and did not debut until late December… and then left for Fiorentina for €4 million about three weeks later. It’s wise to acknowledge a mistake and move on, but Everton essentially wasted a few million Euros.
37. Cristiano Ronaldo, CF, Manchester United
Signed from Juventus for €17 million, 2021-22
By 2021, Cristiano Ronaldo was no longer enhancing the performance of major clubs. A desperate Juventus had acquired him from Real Madrid for a €117 million fee, but their point total declined each season he was there, and the Champions League boost he was expected to provide never materialized. While the transfer fee to bring him back to Manchester United was not particularly burdensome, his salary demands remained substantial.
Ronaldo scored 18 league goals in his only full season back in Manchester, but United dropped from second to sixth in the league, and then-manager Erik ten Hag was uninterested in adjusting his system to accommodate Ronaldo’s increasingly limited skill set. (He could score, but he did not press, and he required the entire attack to be centered around him.) United sold many shirts upon his return, but achieved little else, and his contract was terminated 15 months after his arrival.
36. Ángel Di María, FW, Manchester United
Signed from Real Madrid for €75 million, 2014-15
In the four years prior to his move to Manchester, Di María averaged 5.5 goals and 12.5 assists in league play with Real Madrid. In the five years following his departure from United, he averaged 9.4 goals and 11.2 assists with PSG. However, the most expensive Premier League transfer at that time lasted just one disappointing season at Old Trafford. It began positively—he was named the Premier League’s player of the month in September 2014—but after suffering a hamstring injury in November, his performance declined sharply. He became a scapegoat for United’s underwhelming season under Louis van Gaal, his home was burglarized, and his wife disliked the local cuisine.
This transfer failed in nearly every conceivable way, although it was somewhat redeemed by the solid transfer fee (€63 million) PSG paid to United.
35. Jack Rodwell, DM, Sunderland
Signed from Manchester City for €12.5 million, 2014-15
Rodwell was promising at Everton as a teenager but had minimal impact during two seasons with Manchester City; nonetheless, Sunderland eagerly invested significant money—without a “salary reduction if we get relegated” clause—to bring him to the Stadium of Light in 2014. He was plagued by injuries and did nothing to help the Black Cats avoid relegation in 2017, and he was one of the most expensive players in the second tier while making only two appearances in 2017-18 as Sunderland faced relegation again.
34. Agustin Delgado, FW, Southampton
Signed from Necaxa for €5.8 million, 2001-02
A standout for Ecuador—he scored 31 times in 71 national team appearances, including 13 in 21 matches in 2000-01—Delgado seemingly could not tolerate being so far from home. He played just two matches for Southampton in his first season due to injuries, then frustrated the club after suddenly being fit enough to participate in all three of Ecuador’s World Cup matches (and score against Mexico).
A year after his arrival, Delgado announced he was leaving the club because “it’s clear the coach [Gordon Strachan] dislikes me and South Americans in general.” He then surprised the club by returning shortly afterward, though it did not benefit him much. He scored twice in just 15 appearances before returning to the Ecuadorian Serie A in 2004.
(He would score twice more at the 2006 World Cup.)
33. Roger Johnson, CB, Wolves
Signed from Birmingham City for €8 million, 2011-12
While he is not the most expensive transfer on this list, in terms of return on investment, it is difficult to find a transfer that yielded less. Wolves manager Mick McCarthy quickly made the 6-foot-3 defender the captain upon his arrival, but McCarthy was dismissed in February during a relegation battle, and Johnson reportedly showed up drunk for training in March. He captained a second consecutive relegation the following season as well. He soon left via free transfer, and while Wolves rebounded and ascended back up the English pyramid, Johnson’s career only declined further.
32. Alexander Isak, CF, Liverpool
Signed from Newcastle for €145 million, 2025-26
When a player is signed for such an exorbitant transfer fee, they essentially start on this list and must work to prove otherwise. Isak may eventually do so, but in his first six months with Liverpool, the 26-year-old has scored only three goals in 777 minutes across all competitions and has missed the last two months due to injury. It has been a disastrous beginning for a player who netted 62 goals in three seasons with Newcastle.
31. Jack Grealish, LW, Manchester City
Signed from Aston Villa for €117.5 million, 2021-22
Over four seasons, €117.5 million (and approximately €18 million annually in salary) yielded Manchester City 17 goals and 23 assists. This expenditure did not prevent the high-spending City from winning three Premier League titles and a long-awaited Champions League title in 2022-23—and certainly did not stop Grealish from celebrating that Champions League victory—but when a player is primarily remembered for their performance during a parade, it is clear they did not meet expectations.
30. Juan Sebastian Veron, MF, Manchester United
Signed from Lazio for €42.6 million, 2001-02
Recognizing the need to adapt tactically to remain competitive in Europe, Sir Alex Ferguson’s United made the 26-year-old Veron the most expensive transfer in English history at that time. Two years later, he departed for Chelsea at half the cost. He scored three goals in September 2001 and won the Premier League’s player of the month award, but he would only add five more league goals for the club; Ferguson struggled to integrate his skill set into a talented but perhaps inflexible midfield, and Veron found it more challenging than anticipated to adjust to the game in England.
In fact, one could argue that his transfer to Chelsea should also be included on this list: he was a more established player, and the Blues still paid over €20 million for him.
29. Giannelli Imbula, DM, Stoke City
Signed from Porto for €24.3 million, 2015-16
After two consecutive top-half finishes, Stoke appeared to shift from a scrappy overachiever mentality to making moves like a genuine top club in England. However, things deteriorated rapidly. As yet another club-record signing on this list—someone Marcelo Bielsa once claimed had the potential to become one of the best midfielders in the world—Imbula made only 28 appearances for the club. He showed promise late in 2015-16, but within a year, he was finished. He was loaned out amid concerns about his attitude as Stoke fought relegation, and his contract was terminated early.
