Chelsea and AC Milan have shared a symbiotic relationship over the years, with players frequently swapping the San Siro for Stamford Bridge and vice versa.
This trend has been especially noticeable in recent times, with Milan often signing Chelsea’s young talents or under-utilised stars and transforming them into key players.
Here, we’ve compiled a list of every player who has ever represented both clubs, and some of the names may just surprise you.
Jimmy Greaves
Chelsea (1957–1961), AC Milan (1961)
One of Chelsea's prolific-ever goalscorers, the great Jimmy Greaves scored 132 goals in 169 games for the Blues between 1957 and 1961.
After leaving Chelsea, he moved to AC Milan, where he maintained his incredible scoring rate with nine goals in just 13 games. However, his time in Italy was brief, and he soon returned to London – this time to join Tottenham Hotspur, where he cemented his status as one of England’s greatest-ever strikers.
Ray Wilkins
Chelsea (1973–1979), AC Milan (1984–1987)
A Chelsea legend in every possible way, Ray Wilkins is widely regarded as one of the club's greatest-ever midfielders.
He was clearly loved in Milan, too, with the club describing him as "a serious and meticulous professional" "who boasted"long-range and accurate shots" and "exemplary correctness."
Ruud Gullit
AC Milan (1987–1993, 1994), Chelsea (1995–1998)
At AC Milan, Ruud Gullit cemented himself as one of Europe’s greatest and most versatile players, helping the Rossoneri secure three Serie A titles and two European Cups as a key figure in Arrigo Sacchi’s Total Football revolution.
The Dutchman later saw out his career as a player-manager at Chelsea. While he wasn’t quite the force he once was, his talent remained undeniable.
Marcel Desailly
AC Milan (1993–1998), Chelsea (1998–2004)
Affectionately known as "The Rock" (and no, not the 'Can You Smell What The Rock Is Cooking?' kind), Marcel Desailly was a near-unbreakable force in defense and one of the greatest center-backs to ever play the game.
A serial winner with AC Milan in the 1990s, he moved to Chelsea toward the end of the decade, spending six seasons at Stamford Bridge. During his 222 appearances for the Blues, he lifted both the FA Cup and the UEFA Super Cup.
Samuele Dalla Bona
Chelsea (1999-2001), AC Milan (2002)
Samuele Dalla Bona came through Chelsea's academy and made 73 appearances for the Blues before moving to AC Milan in 2002. Although he only featured 16 times for the Italian giants, he still managed to pick up winners' medals for both Serie A and the Champions League during his brief spell at Milan.
George Weah
AC Milan (1995–2000), Chelsea (loan in 2000)
George Weah remains the only African footballer in history to have won the Ballon d’Or, claiming the prize in 1995 shortly after joining AC Milan.
The Liberian, who later became his country’s president, moved to Chelsea on loan from Milan in January 1999. During his six-month spell in West London, he scored five goals in 15 games, including two in the FA Cup as the Blues went on to lift the trophy.
Carlo Cudicini
AC Milan (1992-1995), Chelsea (1999-2008)
Carlo Cudicini began his career with AC Milan, but made just two appearances for the club before embarking on a journey through Italy, with stints at Como, Prato, Lazio, and Castel di Sangro.
In 1999, he joined Chelsea and went on to make 216 appearances for the Blues, winning the FA Cup and League Cup twice. Cudicini became a fan favorite for his dependable performances in goal, particularly during his time as a backup to Petr Cech.
Brian Laudrup
AC Milan (1993–1994), Chelsea (1998)
Both AC Milan and Chelsea fans could be forgiven for forgetting that Brian Laudrup played for their clubs, as the Danish playmaker made just 18 appearances for the Rossoneri and only 11 for the Blues.
Winston Bogarde
AC Milan (1997), Chelsea (2000-2004)
Winston Bogarde's career was often marred by his lack of appearances and seemingly cushioned lifestyle. After joining AC Milan in 1997, he made only three appearances for the club before moving to Barcelona, where his situation didn't improve, spending much of his time on the bench.
However, it was at Chelsea where his reputation became infamous. Signed during Gianluca Vialli’s tenure, Bogarde made just 12 appearances in four years. Despite the club’s desire to offload him, Bogarde refused to leave, content with his £40,000-per-week wages.
Christian Panucci
AC Milan (1993–1994), Chelsea (2000–2001)
Christian Panucci began his career at AC Milan, where he spent several years before moving on to play for some of Europe's biggest clubs. After stints with Real Madrid and Inter Milan, he joined Chelsea on loan in 2000.
The Italian made just 10 appearances during his sole season at Stamford Bridge.
Hernan Crespo
Chelsea (2003–2008), AC Milan (loan in 2004–2005)
After Roman Abramovich took over Chelsea in 2003, Hernan Crespo was the first big-name striker signed with the Russian’s money, as the Blues paid Inter Milan £16.8 million for the Argentine’s services.
After just one season at Stamford Bridge, Crespo was loaned to AC Milan, where he impressed, but he returned to Chelsea the following year, scoring 13 goals in all competitions to help the club lift the Premier League title.
Andriy Shevchenko
AC Milan (1999–2006, 2008–2009), Chelsea (2006–2009)
Chelsea paid AC Milan £30.8 million – a record fee for an English club at the time – to sign Andriy Shevchenko in the summer of 2006.
Much was expected of the Ukrainian striker after his prolific spell in Italy, where he scored 173 goals in seven seasons, helping Milan win Serie A and the Champions League. However, despite a few standout performances, he never truly lived up to the hype at Stamford Bridge and was loaned back to Milan just two seasons later.
Michael Essien
Chelsea (2005–2014), AC Milan (2014–2015)
Few Chelsea midfielders have ever been as dominant as Michael Essien.
Nicknamed "The Bison" for his strength and relentless playing style, the Ghanaian made 256 appearances for the Blues between 2005 and 2014, scoring 25 goals – including a stunning long-range strike against Arsenal, often regarded as one of the club’s greatest.
Essien joined AC Milan in 2014 but made just 22 appearances before moving on.
Fernando Torres
Chelsea (2011–2015), AC Milan (2014–2015)
Fernando Torres holds a special place in the hearts of many Chelsea fans, thanks to his unforgettable goal against Barcelona in the 2012 Champions League semifinals and his Europa League heroics the following year – even if his overall time at Stamford Bridge was inconsistent.
Chelsea loaned the Spaniard to AC Milan for the 2014/15 season, but his stint in Italy was underwhelming, with just 10 appearances and a single goal before he returned to boyhood club Atletico Madrid.
Alex
Chelsea (2007–2012), AC Milan (2012–2014)
A Brazilian defender as skilled at scoring long-range screamers as he was at stopping attackers, Alex signed for Chelsea in 2004 from Santos but didn’t officially join the club until 2007 due to work permit issues.
He made 134 appearances for the Blues, netting 10 goals – including a few memorable thunderbolts – before moving to Paris Saint-Germain. Later, he joined AC Milan, where he played out the final years of his career.
Alexandre Pato
AC Milan (2007-2013), Chelsea (2016)
Once a man with the world well and truly at his feet, Alexandre Pato was considered one of the most exciting young strikers in the world during his time with AC Milan, scoring 63 goals in 150 appearances and winning the Golden Boy award in 2009.
However, injuries hindered his progress, and after leaving Milan, Pato bounced around various countries. His brief stint at Chelsea saw him make just two appearances, but he managed to score once.
Fabio Borini
Chelsea (2009-11), AC Milan (2017-2020)
Fabio Borini started his career at Chelsea, but was never able to break into the Blues' first-team, and was eventually sold to Liverpool in 2012. He later joined AC Milan, initially on loan, in 2017, going to make 75 appearances for the club and scoring just eight goals.
Fikayo Tomori
Chelsea (2016–2021), AC Milan (2021–present)
A product of Chelsea's youth academy, Fikayo Tomori’s promising career at Stamford Bridge was cut short in 2021 when, after a strong breakthrough season, he was sold to AC Milan for £25 million.
Since then, he has proven to be worth every penny for the Rossoneri, establishing himself as one of the finest central defenders in Serie A and playing a key role in their 2021/22 title-winning campaign.
Marco van Ginkel
Chelsea (2013–2021), AC Milan (loan in 2014–2015)
Marco van Ginkel was on Chelsea's books for nearly a decade but managed only four appearances for the club. The Dutch midfielder spent the 2014/15 season on loan at AC Milan, where he made 18 appearances and scored one goal.
Thiago Silva
AC Milan (2009-2012), Chelsea (2020-2024)
Thiago Silva established himself as one of Europe's top central defenders during his three-season spell at AC Milan between 2009 and 2012.
Many thought his career was winding down when he joined Chelsea in 2020 at 35, following a successful stint with Paris Saint-Germai, but they were, of course, wrong.
The Brazilian arguably produced the best form of his career at Stamford Bridge, helping the club lift the Champions League and Club World Cup in an incredible four years, before returning to his boyhood club Fluminense at age 39.
Alvaro Morata
Chelsea (2017-2019), AC Milan (2024)
Alvaro Morata has played for some of the biggest clubs in the world, including Real Madrid, Atletico Madrid, Juventus, and both Chelsea and AC Milan.
The Spaniard spent two seasons at Stamford Bridge between 2017 and 2019, scoring 24 goals in 72 games, before moving to Atletico Madrid. In 2024, Atleti sold him to Milan.
Olivier Giroud
Chelsea (2018–2021), AC Milan (2021–present)
Though admittedly not the most prolific scorer, Olivier Giroud remains one of the most criminally underrated strikers of the modern era.
The big Frenchman showcased his Midas touch at Chelsea, scoring 39 goals in four seasons after arriving from Arsenal, helping the Blues lift the FA Cup and the Champions League.
After being sold to AC Milan in 2021, he enjoyed similar success in Italy, netting 49 goals in three seasons and, alongside Tomori, playing a starring role in their Serie A triumph during his debut campaign.
Tiemoue Bakayoko
Chelsea (2017–2023), AC Milan (loan in 2018–2019, 2021–2023)
The less said about Tiemoue Bakayoko's time at Chelsea, the better. Signed for £40 million from AS Monaco in 2017, the Frenchman remains one of the club's most underwhelming signings – perhaps best remembered for his disastrous performance against Watford, widely regarded as one of the worst in Premier League history.
He fared slightly better during his three seasons on loan at AC Milan, particularly in 2018/19, when he made 42 appearances across all competitions and was hailed as "devastating" by Milan boss Gennaro Gattuso.
Asmir Begovic
Chelsea (2015-17), AC Milan (2020)
Signed by Chelsea from Stoke City as back-up to Thibaut Courtois in 2015, Asmir Begović made 33 appearances in two seasons for the Blues before being sold to Bournemouth.
In January 2020, the Cherries loaned him to AC Milan, where he made just two appearances before returning to Dean Court.
Ruben Loftus-Cheek
Chelsea (2014–2023), AC Milan (2023–present)
Constant injuries have hampered what could have been an incredible career for Ruben Loftus-Cheek, who, during his rise, looked like he could become one of the most complete midfielders in world football – the Jude Bellingham before Jude Bellingham, if you will.
Still, the Englishman made 155 appearances for Chelsea between 2014 and 2023 before being sold to AC Milan, where he enjoyed a fine debut season, scoring 10 times in 40 games.
Gonzalo Higuain
AC Milan (2018), Chelsea (2019),
The 2018/19 season was certainly an interesting one for Gonzalo Higuain, with the Argentine striker spending the first half of the campaign on loan at AC Milan from Juventus, and the second half on loan at Chelsea.
In total, he scored 13 goals for the two clubs – eight for Milan and five for Chelsea.
Christian Pulisic
Chelsea (2019–2023), AC Milan (2023–present)
"Captain America" joined Chelsea in 2019 from Borussia Dortmund in a deal worth £58 million. While he showed flashes of brilliance during his four years at Stamford Bridge, he never quite seemed able to adapt to the physicality of the English game.
Interestingly, since moving to AC Milan in 2023, he appears to have found his feet, despite Serie A being renowned as one of the most physical leagues in Europe. Pulisic was named in the Serie A Team of the Season for 2023/24.
Tammy Abraham
Chelsea (2016-2021), AC Milan (2024-2025)
Like Tomori and Loftus-Cheek, Tammy Abraham is another product of Chelsea's academy who has found his way to AC Milan.
The English striker made 82 appearances and scored 30 goals for the Blues before being sold to AS Roma in 2021. After two successful seasons in the Italian capital, followed by another hampered by injury, Roma loaned him to Milan for the 2024/25 season.
Joao Felix
Chelsea (2023–2025), AC Milan (loan in 2025)
Joao Felix's Chelsea career has certainly been an intriguing one.
Initially loaned to the Blues from Atlético Madrid in January 2023, he impressed but was sent back to Spain at the end of the season. He then spent a season on loan at Barcelona before Chelsea finally decided to buy him in the summer of 2024, paying Atlético £46 million for his services.
However, just six months and 20 appearances later, the Portuguese forward was loaned to AC Milan.
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