21 Transfer Flops That Shocked the Premier League

January 22, 2025 Rasmus Kristensen

The Premier League has seen some of the most expensive transfers in football history, but not all of them have been successful. Here, we examine 21 of the biggest transfer flops in the league’s history, highlighting their struggles and why things didn’t work out.

Bebé – Manchester United (£7.4 million)

Signed without Sir Alex Ferguson ever seeing him play, Bebé’s transfer remains one of the most baffling in Premier League history. His limited appearances showcased a lack of readiness for top-level football, and he quickly faded into obscurity.

Radamel Falcao – Manchester United (Loan, valued at ~£6 million)

Ramadel Falcao — Marco Iacobucci Epp / Shutterstock.com

Once a world-class striker, Falcao’s time at United was a shadow of his prime. His lack of fitness and sharpness made his loan spell one to forget.

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Anderson – Manchester United (£20 million)

Once a highly-rated midfielder, Anderson failed to live up to expectations due to fitness issues and inconsistent form. His flashes of brilliance were too few and far between.

Lazar Marković – Liverpool (£20 million)

Marković struggled to adapt to the pace and physicality of the Premier League. A series of loan spells followed, but he never managed to break into Liverpool’s plans.

Alberto Aquilani – Liverpool (£20 million)

Brought in to replace Xabi Alonso, Aquilani spent more time injured than on the pitch. His inability to stay fit and perform consistently made him a costly mistake for Liverpool.

Roberto Soldado – Tottenham (£26 million)

The Spanish striker struggled to adapt to the Premier League’s intensity, scoring only a handful of goals. His lack of confidence in front of goal defined his underwhelming time at Spurs.

Alexis Sánchez – Manchester United (Exchange deal, valued at ~£30 million)

Sánchez’s arrival at United was met with enormous hype, but he never found his rhythm. Despite his hefty wages, his performances were lethargic, making him one of the most disappointing signings in recent memory.

Andriy Shevchenko – Chelsea (£30 million)

One of Europe’s most feared strikers, Shevchenko couldn’t replicate his Serie A form in England. His lack of pace and struggles to adapt to the Premier League’s physicality made him a disappointment for Chelsea fans.

Danny Drinkwater – Chelsea (£35 million)

Drinkwater joined Chelsea after winning the league with Leicester but failed to secure regular playing time. A series of injuries and off-field incidents further derailed his career, leaving him as an expensive flop.

Andy Carroll – Liverpool (£35 million)

Carroll’s transfer remains one of Liverpool’s most questionable moves. Injuries and a playing style that didn’t suit the team’s tactics meant the towering striker could never deliver on his promise.

Eliaquim Mangala – Manchester City (£42 million)

Mangala’s defensive errors and lack of composure under pressure made him a liability for City. Despite his price tag, he quickly fell down the pecking order and was eventually offloaded.

Timo Werner – Chelsea (£48 million)

Werner’s goal-scoring prowess in Germany didn’t translate to the Premier League, where he struggled with finishing and decision-making. Though his work ethic was commendable, he left Chelsea after failing to live up to his fee.

Fernando Torres – Chelsea (£50 million)

After a brilliant run with Liverpool, Torres joined Chelsea for a record fee. However, he struggled with confidence and form, scoring only sporadically. Despite a few memorable goals, including one against Barcelona, his overall impact fell far short of expectations.

Angel Di Maria – Manchester United (£59.7 million)

After a promising start, Di Maria’s form dipped dramatically, and he struggled to adapt to life in England. His single season at United ended with a controversial exit, as he pushed for a move to PSG.

Kepa Arrizabalaga – Chelsea (£71 million)

Marta Fernandez Jimenez / Shutterstock.com

As the world’s most expensive goalkeeper, Kepa arrived with high expectations. However, his inconsistency and high-profile errors led to him losing the starting spot and becoming a symbol of Chelsea’s transfer mismanagement.

Jadon Sancho – Manchester United (£73 million)

Jordan Sancho — feelphoto / Shutterstock.com

Sancho arrived with great fanfare after excelling in Germany, but he has struggled to replicate his Dortmund form. Inconsistencies, lack of confidence, and fitness issues have made it hard for him to establish himself in the starting XI.

Paul Pogba – Manchester United (£89 million)

Pogba’s second stint at United was marred by inconsistency, injuries, and off-field distractions. While his talent was evident, his performances often didn’t match his price tag, leading to frustration among fans and management.

Harry Maguire – Manchester United (£80 million)

The world’s most expensive defender has faced relentless criticism for high-profile mistakes and slow decision-making. Despite flashes of leadership, Maguire has failed to justify his massive price tag.

Antony – Manchester United (£85 million)

Antony has struggled to justify his massive fee, with his performances often criticized for lacking end product. His inconsistent displays have raised questions about his long-term potential at United.

Romelu Lukaku – Chelsea (£97.5 million)

Returning to Chelsea with high hopes, Lukaku’s second stint was plagued by inconsistency and fitness issues. His lack of chemistry with teammates and public comments about wanting to return to Inter Milan further alienated fans and management.