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The Italians were a little more experienced after beating City in their North American tour opener. A goal from Samu Chukwueze tipped the balance in favour of Paulo Fonseca's side, who witnessed the debut of Endrick.
Real Madrid lost 1-0 to Milan at Soldier Field in Chicago in the first friendly of their US tour, with Brazilian Endrick getting his first minutes as a Real Madrid player in a team full of notable absentees, from Kylian Mbappe to Vinicius Junior and Rodrygo Goes.
Nigeria's Samuel Chukwueze scored the decisive goal after 56 minutes at Soldier Field to make it two wins out of two for Portuguese coach Paulo Fonseca's Milan, who had been working as a team for longer than Madrid and were brighter on the pitch.
Endrick started and played 45 minutes before Ancelotti made several changes at the break to make way for a host of academy players.
