As of Sunday, July 5, following the eliminations of Brazil and Mexico, AC Milan boasts the highest representation among clubs at the 2026 FIFA World Cup, with seven of its players still in contention as they prepare for the upcoming matches: Portugal vs. Spain and the United States vs. Belgium in the Round of 16. Despite AC Milan’s stellar showing in the tournament, Rossoneri fans felt a sense of loss when Carlo Ancelotti, one of the club’s greatest legends, exited the World Cup. Notably, during his tenure at AC Milan, Ancelotti didn’t enjoy much fortune with the United States either. While AC Milan won the Italian Super Cup on American soil in the summer of 1993, Ancelotti was part of Arrigo Sacchi’s coaching staff for the Italy in preparation for the 1994 FIFA World Cup hosted in the US. That tournament culminated in Brazil defeating Italy in the final at the Rose Bowl in Pasadena.
In a twist of fate, during the Supercoppa Italiana final held in New York in 2003, the same city where Brazil faced an unexpected exit at the hands of Erling Haaland‘s Norway during the 2026 World Cup, Ancelotti was managing AC Milan, who unfortunately lost to Juventus in a penalty shootout. On a different note, Ancelotti’s eight-year tenure as head coach of the Rossoneri (2001–2009) saw him lead the club on numerous summer tours in the United States, taking on some of Europe’s biggest teams such as Chelsea and Manchester United, along with teams from Major League Soccer (MLS). His management solidified AC Milan’s tradition of pre-season tours in the US, fostering a lasting connection that persisted well after his departure. As one of the club’s distinguished former coaches, he often returned for summer friendlies against the Rossoneri while managing teams like Chelsea, Bayern Munich and Real Madrid.
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