Chelsea's best ever signings
Counting down the finest transfer acquisitions in Chelsea's history
One of the most successful clubs in English football, Chelsea have signed plenty of incredible players throughout their history.
From early stars, to integral members of their silverware-winning sides of the 50s and 70s, right through to the glorious modern era, the Blues' transfer business has come up trumps on many an occasion.
Here at FourFourTwo, we've ranked Chelsea's finest signings of all time...
33. Paul Canoville
Signed from non-League Hillingdon Borough for £5,000 in 1981, Paul Canoville starred as Chelsea returned to the top flight by winning the 1983/84 First Division title.
The Blues' first black player, Canoville's time at Stamford Bridge was tainted by racist abuse from his own fans – although he did have most of them singing his name by the end of it thanks to his consistent displays down the left flank.
32. Dan Petrescu
After one season in English football with Sheffield Wednesday, marauding Romanian full-back Dan Petrescu joined Chelsea in the summer of 1995 – and what a great decision it proved to be.
During a five-year spell at Stamford Bridge, Petrescu racked up 207 appearances and was a mainstay of the Blues teams which won the 1996/97 FA Cup under Ruud Gullit, and the 1997/98 League Cup and Cup Winners' Cup under Gianluca Vialli.
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31. Graeme Le Saux
Jersey-born Graeme Le Saux began his career with Chelsea before leaving for Blackburn Rovers in 1993 – but the England left-back was back four years later in a £5m deal – making him the most expensive defender in English football – having helped Blackburn to the 1994/95 Premier League title.
A Second Division champion during his first Blues' spell, Le Saux's second stint at Stamford Bridge brought considerably higher-profile silverware – notably the 1997/98 League Cup and Cup Winners' Cup.
30. Paulo Ferreira
A Champions League winner with Jose Mourinho's Porto in 2004, Paulo Ferreira followed his boss to Chelsea that summer – and played a key role in the Blues' first ever Premier League title triumph in 2004/05.
The Portugal right-back spent the rest of his career at Stamford Bridge, retiring in 2013 as a three-time English champion and with another Champions League winners' medal to add to his collection.
29. Peter Bonetti
The vast majority of Peter Bonetti's 729 Chelsea appearances – among the very most in the club's history – came during his first spell with the Blues, when he starred in FA Cup, League Cup and Cup Winners' Cup victories.
But the legendary goalkeeper, famously nicknamed The Cat for his grace and rapid reflexes, was hugely influential following his return in 1976 (after the briefest of stints Stateside with the St. Louis Stars), immediately helping a young Chelsea team earn promotion back to the top flight.
28. Eidur Gudjohnsen
Arguably Iceland's greatest player of all time, Eidur Gudjohnsen got his chance in English football with second-tier Bolton Wanderers in the late 90s – and the six-foot-one striker joined Chelsea for £4.5m in the summer of 2000.
In his second season with the Blues, Gudjohnsen formed a highly effective partnership with Jimmy Floyd Hasselbaink which yielded 52 goals in all competitions – and he later netted 12 times in Chelsea's maiden Premier League title success.
27. Ruud Gullit
One of the very best players in the world throughout the 80s and early 90s, Ruud Gullit ended his career at Chelsea, joining as a free agent in 1995 and going on to make 63 appearances for the Blues.
Still a superbly classy – and extraordinarily versatile – operator in his mid-30s, the dreadlocked Dutchman had a great time at Stamford Bridge, becoming player-manager ahead of the 1996/97 campaign and guiding Chelsea to victory in that season's FA Cup (marking the club's first major trophy for 26 years).
26. Ian Hutchinson
Signed from Cambridge United in 1968, striker Ian Hutchinson spent the majority of his career with Chelsea, forming a fine striker partnership with Blues legend Peter Osgood which yielded 53 goals during the 1969/70 season.
Hutchinson played a major role in Chelsea's first ever FA Cup triumph that campaign, taking the final to a replay with a late equaliser against Leeds (after being left limping by a hefty Norman Hunter challenge).
25. David Speedie
Scottish striker David Speedie helped fire Chelsea to the 1983/84 Second Division title with 13 goals across the campaign – among 64 he scored for the Blues altogether in all competitions.
A 1982 arrival from Darlington, Speedie – who excelled in the air despite his diminutive stature – linked up superbly with Chelsea icon Kerry Dixon, spending five years at Stamford Bridge.
24. Tommy Baldwin
It was said that Tommy Baldwin was nicknamed the sponge at Chelsea due to his ability to soak up pressure by holding onto the ball in midfield – but apparently, it actually stemmed from his knack for knocking back pints down the pub.
Regardless, the 1966 arrival from Arsenal goes down as one of the Blues' best ever midfielders – and he helped them to League Cup and Cup Winners' Cup in 1970 and 1971 respectively.
23. Pat Nevin
Another Scottish Stamford Bridge legend, Pat Nevin joined Chelsea from Clyde in 1983 and was integral to their 1983/84 Second Division title win, soon endearing himself to fans by chipping in with plenty of goals from the wing.
Nevin ended that season as the Blues' Player of the Year, an award he would collect once again as Chelsea challenged for the First Division title for much of the 1985/86 campaign.
22. Steve Clarke
One of Chelsea's greatest ever right-backs, Steve Clarke amassed 421 appearances for the Blues after joining from St. Mirren in 1988, spending the final 10 years of his career at Stamford Bridge.
Signed for £422,000, Clarke – who was capped six times by Scotland – went trophyless with Chelsea until his final two seasons, when he picked up FA Cup, League Cup and Cup Winners' Cup winners' medals.
He later served as assistant manager to Jose Mourinho and Avram Grant.
21. Peter Sillett
Peter Sillett joins Steve Clarke among the best right-backs Chelsea have ever had, having starred in the Blues' 1954/55 First Division title-winning campaign.
Brought to Stamford Bridge from Southampton in 1953 by manager Ted Drake, Sillett spent nine years as a Chelsea player, making a total of 288 appearances and earning three England caps.
20. Cesar Azpilicueta
A modern Chelsea legend, Cesar Azpilicueta captained the Blues to victory in the 2020/21 Champions League, as well as the 2018/19 Europa League and 2021 Club World Cup.
In fact, the Spain defender won every major trophy on offer during his 11-year stay at Stamford Bridge, racking up 508 appearances and earning the humorous nickname Dave (because his surname was so hard to pronounce, fans claimed).
19. Roberto Di Matteo
Before he coached Chelsea to their maiden Champions League triumph in 2011/12 (along with that season's FA Cup), Roberto Di Matteo was a hugely popular player for the Blues.
The seriously classy Italian deep-lying midfielder joined from Lazio in 1996 and spent the final six years of his career at Stamford Bridge – and he probably would have spent a fair few more there had injury not forced him to retire aged only 31.
18. Dennis Wise
One of Chelsea's most decorated captains of all time, Dennis Wise wore the armband as the Blues got their hands on two FA Cups, the League Cup and Cup Winners' Cup between 1997 and 2000.
A club-record arrival when he joined from Wimbledon for £1.6m in 1990, the thoroughly tenacious England midfielder featured 445 times for the Blues and was voted Player of the Season on two occasions.
17. Jimmy Floyd Haselbaink
Among the best centre-forwards in Europe during his prime, Jimmy Floyd Hasselbaink first made his mark on the Premier League at Leeds, joining Chelsea in 2000 after a prolific one-season stint in Spain with Atletico Madrid.
Having shared the 1998/99 Golden Boot with Michael Owen and Dwight Yorke, the Dutchman – who possessed great free-kick ability – won it outright in his first campaign with the Blues, notching 23 goals in successive campaigns, and forming a strong striker partnership and friendship with Eidur Gudjohnsen.
16. Ricardo Carvalho
Like Portuguese compatriot Paulo Ferreira, Ricardo Carvalho followed Jose Mourinho from Porto to Chelsea as a 2003/04 Champions League winner – and he only enjoyed even more success in England.
A titan at the back as the Blues conceded just 15 goals en route to the 2004/05 Premier League title, Carvalho was among the finest centre-halves of his era and made 210 Chelsea appearances in all – also helping them to FA Cup and League Cup glory.
15. Kerry Dixon
With 193 goals to his name in all competitions, Kerry Dixon is one of Chelsea's all-time leading scorers – and he banged in 70 of those during his first two seasons at the club, firing the Blues to the 1983/84 Second Division title.
Signed from Reading, Dixon – who found the net four times in eight caps for England during the mid-80s – is an undisputed Chelsea legend.
14. Marcel Desailly
A Champions League winner with Marseille and AC Milan in back-to-back seasons during the early 90s, Marcel Desailly had just starred in France's 1998 World Cup victory when he joined Chelsea from Milan for £4.6m.
One of the world's top defenders at the time, Desailly won the 1999/2000 FA Cup with the Blues and was club captain for most of his six-year spell at Stamford Bridge.
13. George Hilsdon
The first player to score 100 goals for Chelsea, George Hildson joined the Blues from West Ham in 1906 – and returned to the Hammers six years later after netting 108 times in 164 games.
Capped eight times by England – for whom he banged in an extraordinary 14 goals – Hilsdon fired Chelsea to promotion top the top-flight in just the club's second year as a professional outfit.
12. Charlie Cooke
Charlie Cooke gained legendary status across two spells with Chelsea, where he tasted victory in the FA Cup and Cup Winners' Cup in successive seasons (1969/70 and 1970/71).
First signed from Dundee in 1966, the 16-cap Scotland winger left the Blues for Crystal Palace in 1972 – only to return two years later and help them to promotion from the Second Division in 1977 having been relegated from the top flight two years earlier.
11. Michael Essien
An all-time great of African football, Ghanaian icon Michael Essien broke Chelsea's transfer record when he completed his £24.4m move from Lyon in the summer of 2005.
And it would prove to be money exceptionally well spent by the Blues: Essien was an invaluable presence in midfield, winning the Premier League title in 2005/06 under Jose Mourinho and in 2009/10 under Carlo Ancelotti.
He didn't score that many goals – but when he did find the net, it was often spectacular (case in point: this screamer against Arsenal in 2006).
10. Arjen Robben
One of the finest wingers of all time, Arjen Robben tied many a full-back in knots during his career – of which he spent three trophy-laden years with Jose Mourinho's Chelsea.
Brought to Stamford Bridge from PSV in the summer of 2004, the devastating Dutchman made the PFA Premier League Team of the Year as he played a pivotal part in the Blues' title-winning 2004/05 campaign – with his contribution highlighted by the fact injury restricted him to only 18 appearances.
He was it again the following season, collecting another Premier League winners' medal.
9. Ashley Cole
England and Chelsea's greatest left-back of all time, Ashley Cole made the cross-London switch from Arsenal to Stamford Bridge for a mere £5m in the summer of 2006.
That transfer has to go down as one of the most incredible bargains ever: Cole spent eight glorious years with the Blues, winning every major trophy available – including the Champions League in 2011/12 – and being named Chelsea's Players' Player of the Year on two occasions.
8. Gianluca Vialli
The late Gianluca Vialli didn't need long to make himself a legend at Chelsea, immortalising himself at Stamford Bridge in the space of three years.
Once the world's most expensive player, Vialli joined the Blues from Juventus in 1996 and would retire with the West Londoners – finishing up as their player-manager.
In the latter role, the hugely gifted Italian striker – who scored 21 goals for Chelsea – was an FA Cup, League Cup and Cup Winners' Cup winner, during an immensely successful period around the turn of the century for the Blues.
7. Gianfranco Zola
Gianluca Vialli's compatriot and contemporary, Gianfranco Zola was a pure delight to watch, spending seven wonderful years with Chelsea after joining from Parma in 1996.
Winner of the prestigious FWA Footballer of the Year award in 1997 and twice the Blues' Player of the Year, the pint-sized magician was integral to the FA Cup, League Cup and Cup Winners' Cup triumphs.
A scorer of truly stunning goals, Zola found the net 80 times for the Blues in all – including with this memorably audacious flick in an FA Cup clash against Norwich.
6. Claude Makelele
So exceptional at the base of Chelsea's midfield was Claude Makelele that the holding midfield role came to be known colloquially as the Makelele Role.
The Blues' 95-point, 15-goals-conceded Premier League title win of 2004/05 just wouldn't have happened without the mightily dogged Frenchman, who brought a certain glamour to one of the most unglamorous responsibilities on the pitch.
Very, very rarely on the scoresheet, memorably, on the day Chelsea received the Premier League trophy in 2005, Makelele was allowed to take a penalty against Charlton – which he saw saved, only to tuck in the rebound.
5. Petr Cech
The finest goalkeeper in Chelsea's history and perhaps the best the Premier League has ever seen, Petr Cech was a world-class last line of defence for the Blues between 2004 and 2015.
Signed from Rennes for £7m, the Czech Republic legend went on to make 494 appearances for Chelsea, lifting every major honour – and continuing to perform to an elite level after recovering from the horrific head injury he sustained against Reading in 2006, resulting in him notably wearing a rugby-style headguard for the rest of his career.
4. Didier Drogba
A nightmare-and-a-half for defenders, the deadly Didier Drogba became the first African player to score 100 Premier League goals, registering 164 times for Chelsea in all competitions across two spells.
During his first stint at Stamford Bridge, the iconic Ivorian scooped the Golden Boot on two occasions, with his most prolific campaign coming in 2009/10 – when he netted 29 times (and 37 in all competitions) as Carlo Ancelotti steered the Blues to the double.
After scoring an equaliser to take the 2012 Champions League final against Bayern Munich to extra time, and then Chelsea's decisive shootout penalty, Drogba left as a free agent – only to return and add a fourth Premier League winners' medal in 2014/15.
3. Roy Bentley
Skipper of Chelsea's first ever top-flight title-winning team in 1954/55, Roy Bentley's name really is the stuff of legend at Stamford Bridge – and he did much more than just wear the captain's armband.
Signed from Newcastle in 1948 for £11,000, Bentley went on to rack up 152 goals for the Blues – including a career-best 22 in that glorious 1955/55 First Division campaign.
Capped 12 times by England, netting nine times, the striker was Chelsea's record goalscorer when he left for local rivals Fulham in 1956 – and he remains towards the very top of their list of all-time leading marksmen.
2. Eden Hazard
Chelsea's finest foreign import of all time, Eden Hazard was nigh-on impossible to play against at his peak, tearing apart many a Premier League defence during his seven years at Stamford Bridge – where he established himself as one of the best players on the planet.
A 2014/15 and 2016/17 Premier League champion, the phenomenally fast, tremendously tricky Belgian scored 110 goals for Chelsea – none more notable than his outrageous solo effort against Arsenal in 2017, one of the great Premier League goals – was voted PFA Players' Player of the Year in 2015.
1. Frank Lampard
If Frank Lampard is not Chelsea's greatest player of all time (and John Terry is the only man who can really challenge him for that honour), he's certainly their best ever signing.
Picked up for £11m in the summer of 2001, Lampard went from brilliant box-to-box midfielder to an all-round attacking threat, sensationally scoring 22 Premier League goals in 2009/10 – when he won his third and final English title.
A European champion in 2011/12, the 106-cap England international left Stamford Bridge in 2014 as the Blues' record goalscorer after netting 211 times altogether in 648 appearances.
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Tom Hancock started freelancing for FourFourTwo in April 2019 and has also written for the Premier League and Opta Analyst, among others. He supports Wycombe Wanderers and has a soft spot for Wealdstone. A self-confessed statto, he has been known to watch football with a spreadsheet (or several) open...
