Players who played for Chelsea and AC Milan
- Ruben Loftus-Cheek is the latest star to swap Chelsea for AC Milan
- Jimmy Greaves was the first direct transfer between the two European giants
- Stars like Fernando Torres and Thiago Silva have played for both
Two grand footballing institutions have forged quite the connection over the years.
Contemporary behemoths Chelsea and the historically significant AC Milan have enjoyed the talents of some of the game's all-time greats, some of whom have suited up in both west London and Italy's fashion capital.
While far from an all-timer, Ruben Loftus-Cheek, who promised so much before a serious Achilles injury suffered in 2019 tamed his lofty trajectory, will be the latest to suit up for both clubs after he completed a £15m move to the Rossoneri.
Here's a list of all the players to play for Chelsea and Milan.
Players who have played for both Chelsea and AC Milan
Player | Years at both clubs | Chelsea appearances | Milan appearances |
|---|---|---|---|
Jimmy Greaves | Chelsea (1957-1961) / Milan (1961) | 84 | 13 |
Ray Wilkins | Chelsea (1973-1979) / Milan (1984-1987) | 179 | 105 |
Brian Laudrup | Milan (1993-1994) / Chelsea (1998) | 11 | 18 |
Marcel Desailly | Milan (1993-1998) / Chelsea (1998-2004) | 221 | 186 |
Ruud Gullit | Milan (1987-1993,1994) / Chelsea (1995-1998) | 58 | 171 |
George Weah | Milan (1995-2000) / Chelsea (2000) | 15 | 147 |
Winston Bogarde | Milan (1997) / Chelsea (2000-2004) | 12 | 4 |
Christian Panucci | Milan (1993-1996) / Chelsea (2000-2001) | 10 | 134 |
Carlo Cudicini | Milan (1992-1995) / Chelsea (1999-2009) | 216 | 3 |
Sam Dalla Bona | Chelsea (1999-2002) / Milan (2002-2006) | 73 | 16 |
Hernan Crespo | Chelsea (2003-2008) / Milan (2004-2005) | 73 | 40 |
Andriy Shevchenko | Milan (1999-2006, 2008-2009) / Chelsea (2006-2009) | 77 | 322 |
Michael Essien | Chelsea (2005-2014) / Milan (2014-2015) | 256 | 22 |
Fernando Torres | Chelsea (2011-2015) / Milan (2014-2016) | 172 | 10 |
Alexandre Pato | Milan (2007-2012) / Chelsea (2016) | 2 | 150 |
Alex | Chelsea (2004-2012) / Milan (2014-2016) | 134 | 48 |
Marco van Ginkel | Chelsea (2013-2021) / Milan (2014-15) | 4 | 18 |
Mario Pasalic | Chelsea (2014-2020) / Milan (2016-2017) | 0 | 27 |
Fabio Borini | Chelsea (2009-2011) / Milan (2017-2020) | 8 | 75 |
Tiemoue Bakayoko | Chelsea (2017-2023) / Milan (2018-2019, 2021-2023) | 43 | 63 |
Gonzalo Higuain | Milan (2018-2019) / Chelsea (2019) | 18 | 22 |
Asmir Begović | Chelsea (2015-2017) / Milan (2020) | 33 | 2 |
Thiago Silva | Milan (2009-2012) / Chelsea (2020-present) | 117 | 119 |
Olivier Giroud | Chelsea (2018-2021) / Milan (2021-present) | 119 | 85 |
Fikayo Tomori | Chelsea (2016-2021) / Milan (2021-present) | 27 | 107 |
Ruben Loftus-Cheek | Chelsea (2014-2023) / Milan (2023-present) | 155 | 0 |
Jimmy Greaves
Prolific forward Jimmy Greaves was the first player to make a direct transfer between Chelsea and Milan. After spending four years with the Blues, Greaves ventured off to Lombardy but his stint was quiet and brief.
The Englishman never saw eye-to-eye with catenaccio pioneer Nereo Rocco and returned to England after just a year in Italy.
Ray Wilkins
On the contrary, Ray Wilkins loved life at San Siro. The midfielder emerged as a key performer during his four years at the club, but his time in Milan arrived just before they ascended to new heights under Arrigo Sacchi.
Wilkins had started out at Chelsea, his boyhood club, and made 179 appearances for the Blues.
A relaxation in the rules surrounding limitations on foreign players sparked an upsurge in overseas transfers in the 1990s and the Premier League emerged as a hub for elite foreign talent following Serie A's golden era. The likes of Marcel Desailly, Ruud Gullit, George Weah and Andriy Shevchenko swapped Milan for Chelsea on either side of the millennium, while Hernan Crespo was signed by the Blues from Inter as one of the first major signings of the Roman Abramovich era.
The Argentine enjoyed a mixed spell at Stamford Bridge and was loaned to Milan for the 2004/05 season.
After Shevchenko left Chelsea in 2009 following a difficult Premier League career, the names that connect the two clubs haven't been quite as glamorous. Marco van Ginkel, Mario Pasalic, Fabio Borini, Tiemoue Bakayoko and Asmir Begovic have all donned the jerseys of both clubs over the past decade.
Gonzalo Higuain enjoyed an indifferent time of it at both clubs, while Alexandre Pato was well on the decline by the time he joined Chelsea in 2016. Thiago Silva, on the other hand, has been nothing short of exceptional in west London after leading Milan to Serie A glory in 2011.
As for Loftus-Cheek, he'll be looking to follow in the footsteps of Fikayo Tomori and Olivier Giroud, who have both forged stellar careers at Milan after leaving Chelsea.
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