AC Milan and Chelsea will meet on the pitch for the first time in 13 years at Stamford Bridge on Wednesday night, but there has been plenty of meetings off the field since.
La Gazzetta dello Sport hypothesises that the next operation completed between the two clubs could be Rafael Leao, but the first was in 1961 when Jimmy Greaves – who had scored 132 goals in 169 games with the Blues – moved to the Milan side with Nereo Rocco and Cesare Maldini. The move did not work out for the English striker as he left Milan after only six months after 9 goals in 13 appearances.
In the late 1990s and early 2000s it was time for Chelsea to sign some players from Milan. Centre-back Marcel Desailly was the first to make the switch in 1998 – after winning the World Cup with France.
Samuele Dalla Bona, on the other hand, made the reverse journey from Chelsea to Milan in the summer of 2002. After 73 games he returned to Italy and won the Champions League.
Hernan Crespo was at Chelsea in 2003-04, at Milan the following season and then went back to the west London club before signing for Inter. The Argentine was joined by Andriy Shevchenko at Chelsea in 2006 as he moved to the London capital for €45m. The Ukrainian striker will return on loan to Milan in 2008-09.
The 2010s did not feature such high-profile names. Marco van Ginkel – a Dutch midfielder bought by the Blues for €10m in 2013 – joined Pippo Inzaghi’s Milan in 2014-15 and scored one goal in 18 games.
Fernando Torres and Michael Essien arrived together with Van Ginkel but their best days were behind them. The Spaniard scored only once and went back to Atletico Madrid after six months, while the Ghanian played 22 games.
Mario Pasalic was on loan to the Rossoneri from Chelsea during the 2016-17 season, scoring five goals in 24 matches and he is now at Atalanta. Another player who played for both was Gonzalo Higuain, who was on loan at Milan in 2018-19 which was cancelled after six months, and then he went to Chelsea.
Three former Chelsea players are in the squad at the moment with the first being Tiemoué Bakayoko, who initially joined in 2018-19 under Gennaro Gattuso and has not had a successful return.
Fikayo Tomori arrived in January 2021 and was immediately decisive, earning a permanent move after a loan for half a season. Finally, there is Olivier Giroud, the man who broke the curse of the No.9 and would love to show Graham Potter’s men what they are missing.
