CARLO MEMORIES | OneFootball

Following the eliminations of Brazil and Mexico, as of Sunday 5 July, AC Milan remained the best-represented Italian club at the 2026 FIFA World Cup, with seven Rossoneri players still competing ahead of the Portugal v Spain and United States v Belgium Round of 16 matches. Beyond AC Milan's strong representation in the tournament, however, Rossoneri fans were particularly saddened by the World Cup exit of one of the club's greatest icons, Carlo Ancelotti. Interestingly, even during his time with the Rossoneri, the United States never brought Carletto much joy. AC Milan did lift the Italian Super Cup on American soil in the summer of 1993, but Ancelotti was then part of Arrigo Sacchi's Italy coaching staff, preparing for the 1994 FIFA World Cup in the United States. That tournament ultimately ended with Brazil defeating the Azzurri in the final at the Rose Bowl in Pasadena, Los Angeles.

When the Supercoppa Italiana final was held in New York in 2003, ironically, the same city where Brazil were knocked out by Erling Haaland's Norway at the 2026 World Cup, Ancelotti was in charge of AC Milan. The Rossoneri were beaten on penalties by Juventus. Pre-season friendlies have been slightly different. During his eight years as head coach of the Rossoneri (2001–2009), Ancelotti led the club on several summer tours of the United States, facing some of Europe's biggest clubs, including Chelsea and Manchester United, as well as teams from Major League Soccer (MLS). Under his management, travelling to the United States for pre-season preparation became a regular part of AC Milan's summer schedule. His connection with AC Milan in the US continued long after his departure. As one of the club's greatest former coaches, he returned on several occasions to face the Rossoneri in summer friendlies while in charge of Chelsea, Bayern Munich and Real Madrid.

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