 Maldini's father Cesare also played for and captained Milan, and was a successful national under-21 manager, who also coached Milan and the senior national side during the 1998 World Cup.Originally a Milan youth squad product, Maldini also went on to play his entire club career with the Milan senior side.He won the Coppa Italia Primavera with the Milan Youth side during the 1984–85 season, and he made his league debut for Milan under manager Nils Liedholm during the same season on 20 January 1985, replacing the injured Sergio Battistini in a match against Udinese at age 16.