Chelsea’s worst Premier League signings of all time

Chelsea's transfer record across the Premier League era is enviable by almost any measure, with five league titles since 1992, two Champions League triumphs and a long list of era-defining arrivals helping establish the club as one of English football's superpowers.

Even after many permanent deals, though, the Blues have had their share of expensive mistakes, whether the problem was an inflated fee, poor performances, controversy, or a player simply failing to settle in England.

Wesley Fofana and Alvaro Morata are among the honourable mentions, but the 10 below represent some of the clearest cases of Chelsea getting their recruitment badly wrong.

Chris Sutton

Chris Sutton's £10m move from Blackburn Rovers in the summer of 1999 made him Chelsea's record signing, with the striker having previously won the Premier League title alongside Alan Shearer in 1995.

The goals that had made Sutton such a feared forward at Ewood Park simply did not follow him to Stamford Bridge, as he scored just once in 28 Premier League appearances during his only season in west London.

He was sold to Celtic the following summer, leaving Chelsea with a record signing who had managed only one league goal and one of the most underwhelming big-money spells in the club's history.

Baba Rahman

Baba Rahman arrived from Augsburg for a reported £14m in August 2015, with the fee potentially rising to £22m through add-ons as Chelsea looked to secure a long-term option at left-back.

The Ghana international had impressed in the Bundesliga, but opportunities were hard to come by under Jose Mourinho and he never managed to make the position his own at Stamford Bridge.

Rahman made only 23 appearances for Chelsea across eight years on the books, with most of those coming in his first season before loan spells at Schalke, Reims, Mallorca, PAOK and Reading took him away from West London.

Winston Bogarde

Winston Bogarde joined Chelsea on a free transfer from Barcelona in the summer of 2000, bringing Champions League-winning pedigree from his time at Ajax and further European experience from his spell with the Catalan giants.

His time at Stamford Bridge could hardly have been more different, with the defender making just 12 appearances in four years, 11 of them during his first season.

Bogarde became notorious for refusing to leave despite limited first-team opportunities, later admitting that money was a major reason for staying, with his reported £40,000-a-week contract adding to the controversy surrounding his spell.

Tiemoue Bakayoko

Tiemoue Bakayoko's £40m move from Monaco in the summer of 2017 looked like a statement signing, with the midfielder arriving after helping his side win Ligue 1 and reach the Champions League semi-finals.

Things went downhill quickly, however, as Bakayoko struggled with the pace of English football and finished his only full Chelsea season with 43 appearances and just three goals.

The Frenchman was sent on loan to AC Milan the following campaign and later had spells at Monaco and Napoli, eventually leaving Chelsea without making another first-team appearance after his debut season.

Danny Drinkwater

Danny Drinkwater joined Chelsea from Leicester City for £35m in the summer of 2017, just over a year after playing a key role in one of the most extraordinary title wins in Premier League history.

The hope was that he could bring some of that Leicester magic to Stamford Bridge, but the midfielder struggled to break into the side and made only 23 appearances during his five years at the club.

He subsequently spent time on loan at Burnley, Aston Villa, Kasimpasa and Reading, meaning Chelsea paid £35m for a player who ultimately contributed very little in a blue shirt.

Andriy Shevchenko

Andriy Shevchenko's £30m move from AC Milan in the summer of 2006 was one of Roman Abramovich's biggest statements yet, with the Ballon d'Or winner arriving after years of terrorising Serie A defences.

The move never produced the same Shevchenko, though, as the Ukrainian managed just 22 goals in 77 appearances across three seasons and struggled to adapt to the pace and physical demands of English football. He eventually returned to Milan on loan, but could not rediscover his best form before his Chelsea career came to an end.

Fernando Torres

Fernando Torres's £50m move from Liverpool in January 2011 broke the British transfer record, with Chelsea bringing in a striker who had been among the most feared forwards in Europe during his time at Anfield.

The goals dried up almost immediately, with Torres scoring just 45 times in 172 appearances for Chelsea and enduring a lengthy Premier League run without finding the net.

There were some unforgettable moments along the way, most notably his Champions League semi-final goal against Barcelona, and he ended his Chelsea career with Champions League and Europa League winners' medals, though those achievements could not disguise how far his overall output fell short at the West London club.

Mykhailo Mudryk

Mykhailo Mudryk's £88.5m move from Shakhtar Donetsk in January 2023 became one of the most eye-catching transfers of the season, with Chelsea beating Arsenal to the highly-rated winger after a dramatic pursuit.

The Ukrainian showed flashes of his blistering pace, but consistent end product proved much harder to find, with 10 goals in his first 73 appearances leaving him well short of the standard expected from such an expensive signing.

A doping case then brought another setback, with Mudryk provisionally suspended in December 2024 and later handed a four-year ban, although the case was resolved in July 2026 and he is now free to return to competitive football.

Romelu Lukaku

Romelu Lukaku's first spell at Chelsea was easy enough to explain away given that he was a teenager, but his £97.5m return from Inter Milan in the summer of 2021 was supposed to be very different.

The Belgian had just helped Inter win Serie A and arrived as the proven goalscorer Chelsea had been missing, though he managed only eight goals in 26 Premier League appearances during his second spell.

His relationship with Thomas Tuchel's system never quite clicked, and the situation deteriorated further after an interview in which Lukaku criticised his circumstances and made clear his desire to return to Inter.

He was loaned back to the Italian club that season, followed by another temporary spell at Roma before Napoli eventually signed him permanently in 2024.

For £97.5m, eight Premier League goals and a controversial second spell represented a remarkably poor return, making Lukaku one of Chelsea's most expensive mistakes.

Kepa Arrizabalaga

Kepa Arrizabalaga's £71.6m move from Athletic Bilbao in the summer of 2018 made him the most expensive goalkeeper in football history, setting a benchmark that was always going to bring enormous scrutiny.

The Spaniard made 163 appearances for Chelsea across five seasons, but consistency was rarely his strongest suit and he was repeatedly dropped by different managers during his time at Stamford Bridge.

Kepa’s most infamous moment came in the 2019 League Cup final against Manchester City, when he refused to leave the pitch after Maurizio Sarri had attempted to substitute him before the penalty shootout.

There were better moments, including his role in Chelsea's 2020-21 squad that won the Champions League, but they never fully erased the concerns surrounding his performances or the extraordinary fee paid for him.