In 1993, Orlando was purchased by Italian and European giants A.C. Milan for 3.2 billion Lit. With the club, he made 15 appearances in Serie A under manager Fabio Capello, and 6 in the UEFA Champions League, as Milan went on to win both competitions, as well as the Supercoppa Italiana; he notably managed a goal in the Champions League, scoring in Milan's 6–0 away victory over FC Copenhagen. Orlando also made 4 appearances in the Coppa Italia that season for Milan, making 25 appearances in total in all competitions.