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Riccardo Montolivo won the Supercoppa Italiana with AC Milan in 2016. The Supercoppa Italiana is a one-off match between the winners of the Serie A and the Coppa Italia. Montolivo was the captain of AC Milan at the time, and he led the team to a 2-1 victory over Juventus in the final. This was AC Milan's first Supercoppa Italiana title since 2007.