The Magnificent Eight: Exceptional Players Who Represented AC Milan and Chelsea
Chelsea and AC Milan have conducted regular business with one another in recent transfer windows and a strong working relationship has continued this summer.
Ruben Loftus-Cheek has completed a transfer from Chelsea to the Italian giants, while the two clubs are negotiating a deal for Christian Pulisic to follow his former team-mate to the San Siro.
That duo look set to join an extensive list of star names to have represented both clubs, with a number of iconic footballers having worn the colours of each side.
Here are eight brilliant players who played for both AC Milan and Chelsea.
Jimmy Greaves is recognised as one of English football’s greatest ever goalscorers and announced his arrival as one of the finest forwards in the game at Chelsea.
Greaves scored 124 league goals across just four seasons with Chelsea after progressing from the club’s ranks, including a 41-goal league campaign in 1960/61 season – the highest recorded since the Second World War.
Greaves’ goals attracted interest from AC Milan and an £80,000 deal was agreed for the predacious forward. It was a deal that appeared to suit all parties, with Greaves given a chance to win silverware at the San Siro and the fee received easing Chelsea’s financial issues.
However, Greaves struggled to adapt in Milan and endured a difficult relationship with head coach Nereo Rocco, who had replaced previous manager Giuseppe Viani soon after the deal for Greaves was agreed.
Greaves lasted just four months at Milan, in which he scored nine goals in 13 appearances but had disdain for life in Serie A. He returned to England to sign for Tottenham and went on to become an all-time great in north London, scoring 268 goals in 381 games. His career return of 357 top-flight goals is a record in English football.
Ruud Gullit signed for AC Milan for a world-record fee from PSV Eindhoven in the late eighties, forming part of a Dutch trio that became the driving force of the club’s successes under Arrigo Sacchi.
Gullit was named as winner of the Ballon d’Or in 1987 and helped Milan end a nine-year wait for the Scudetto during his debut campaign.
Starring alongside compatriots Marco van Basten and Frank Rijkaard, Gullit won three league titles and back-to-back European Cups during his time with Milan, earning a reputation as one of the most influential players in Europe with a powerful physique, versatility, and aerial threat.
Gullit’s career also saw him win the 1988 European Championship with the Netherlands and saw the Dutchman star at centre-forward, midfield and as a sweeper – producing world-class levels in each position.
He signed for Chelsea after a short spell at Sampdoria and was the catalyst for a revolution in west London. The first marquee name to sign for Chelsea in the Premier League era, his arrival ushered in a new dawn as exciting foreign imports arrived to transform the Blues from mid-table mediocrity to challengers in cup competition.
Gullit later took over on a player-manager basis and was responsible for the recruitment of Gianfranco Zola and Gianluca Vialli among others, while he became the first foreign manager to win the FA Cup in 1996 – ending Chelsea’s 26-year wait for a major trophy.
George Weah is the second of three Ballon d’Or winners to feature on this list, after becoming the first African – and so far only – to win football’s most prestigious individual accolade.
After impressive spells in France with Monaco and Paris Saint-Germain, Weah signed for AC Milan in 1995. He was named as the FIFA World Player of the Year and Ballon d’Or winner after ending his final campaign at PSG as the Champions League’s leading scorer and made an immediate impact after his move to Milan.
Weah formed part of a formidable forward line alongside Roberto Baggio and Dejan Savićević as Milan won the Scudetto during his debut season. He added a second Serie A title in 1998/99 and produced several moments of individual brilliance in the colours of the Rossoneri. Among his most notable was a sensational coast-to-coast goal against Hellas Verona at the San Siro, in which Weah picked up possession just outside his own area before running the length of the pitch to score.
Weah signed on loan for Chelsea during the second half of the 1999/2000 campaign and scored five goals in 15 appearances for the Blues, including a debut winner against Tottenham. Despite being past his peak, he contributed to a campaign that saw Chelsea win the FA Cup.
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Marcel Desailly signed for AC Milan after forming part of the Marseille team who defeated the Italians in the 1993 Champions League final.
His first season saw Desailly impress to become the first player to win back-to-back European Cups with different teams, as the marauding midfielder scored the fourth goal in Milan’s famous 4-0 win over Johan Cruyff’s Barcelona in Athens. The Rossoneri also won Serie A, conceding just 15 goals in the process.
Desailly won a second league title in 1995/96 and made 186 appearances for Milan, before signing for Chelsea in search of a new challenge. The Frenchman settled in his preferred centre-back role in west London and went on to become a much-loved figure at Stamford Bridge.
He won the FA Cup in 2000 and formed a fine centre-back partnership with compatriot Frank Leboeuf. Desailly was later named captain at Chelsea and ‘The Rock’ remains one of the club’s all-time greats after 222 appearances in all competitions. The defender – who formed part of France’s World Cup-winning team in 1998 – was a key figure in mentoring an emerging John Terry.
Roman Aramovich’s arrival at Chelsea transformed the club’s fortunes overnight and the Russian’s first summer in charge led to mass change and marquee imports.
Among them was Hernan Crespo, signed for a cool £16.8m from Inter Milan after a successful career in Italy that saw the forward fire goals for star-studded teams at Parma, Lazio and Inter, with a world-record move in between.
Crespo became Claudio Ranieri’s 11th signing of the summer but struggled to live up to expectations. He scored 12 goals in 32 appearances during his debut campaign but was allowed to leave on loan for AC Milan after the arrival of Jose Mourinho and Didier Drogba in 2004.
Crespo formed a fine partnership with Andriy Shevchenko and scored 17 goals in all competitions as Milan reached the Champions League final, in which the Argentine netted a brace in defeat to Liverpool.
Chelsea recalled the forward the following season and he won the first top-flight title of his career in 2005/06, before departing west London with a record of 25 goals in 73 appearances to re-join Inter.
Milan’s successful side of the early noughties was full of talent, a wonderful side spearheaded by the brilliance of Andriy Shevchenko. There was arguably no finer finisher in Europe than the Ukrainian at that time, with Shevchenko earning iconic status in Milan after his arrival from Dynamo Kyiv.
Shevchenko had tormented defences as part of Dynamo Kyiv’s superb side under Valeriy Lobanovski before signing for Milan in a club-record deal.
Across seven seasons he scored 173 goals in all competitions and won a host of honours, lifting Serie A, the Coppa Italia and Champions League with the Rossoneri and twice ending seasons as Italy’s leading scorer.
In 2004 he was named as winner of the Ballon d’Or after a 29-goal campaign, performances which led to Chelsea breaking the British transfer record to secure his services two seasons later.
Shevchenko signed for Chelsea in a £30.8m deal but struggled to find his form during a difficult time in the Premier League. He spent two seasons at Chelsea and won the FA Cup, but scored a modest 22 goals in 77 appearances.
He returned to AC Milan in a disappointing loan move before ending his career back at Dynamo Kyiv. Only Gunnar Nordahl has ever scored more goals for AC Milan.
Michael Essien’s box-to-box brilliance saw Chelsea spend big to sign the midfielder from Lyon, with the Ghana international arriving in the Premier League as Ligue 1’s reigning Player of the Season.
He became an instant fans’ favourite for his powerful performances in the club’s engine room, with Essien a footballer who used every ounce of effort to outrun the opposition midfield. His first season ended in Premier League title success and Essien won eight major trophies across his eight seasons at Stamford Bridge.
His dynamism made Essien one of the standout names in the Premier League at his best, before fitness issues plagued his latter time with the club. Essien signed for AC Milan after a short loan spell at Real Madrid, but the Italian side saw only glimpses of the talent who had been a rampaging force during his Premier League peak.
Thiago Silva is what is known in football as a late bloomer. The centre-back’s career had been modest until a move to AC Milan in his mid-twenties, a transfer which kickstarted an evolution to one of the best centre-backs of his era.
Silva spent three seasons in the colours of the Rossoneri and won the Serie A title in 2010/11, with the athleticism and anticipation of the Brazilian a fine compliment to the ageing Alessandro Nesta alongside him.
The defender’s performances saw him included in the Serie A Team of the Year in consecutive campaigns, before Paris Saint-Germain signed Silva and team-mate Zlatan Ibrahimovic in a combined deal worth €62m.
That fee provided inspired as the duo inspired the most successful era in the club’s history, with Silva winning seven league titles, 11 domestic cups and inclusion in Ligue 1’s Team of the Year in eight straight seasons.
After his contract was surprisingly not renewed, Silva signed for Chelsea on a free transfer in 2020. Despite reservations over his age and ability to handle the physical demands of the Premier League, the Brazilian has proven an inspired purchase. Silva won the Champions League during his debut campaign and was named as Chelsea’s Player of the Season, aged 38, in 2022/23. A firm fan favourite after a period of evergreen class at Stamford Bridge.