He began the following season with Milan, but was sold to Juventus at the end of the transfer window in exchange for creative forward and attacking midfielder Paolo Di Canio. Orlando made 13 appearances for the Turin club in Serie A that season, serving as a back-up to Robert Jarni, as he managed to win his second consecutive Serie A title. He also managed to capture the Coppa Italia with Juventus that season, making 5 appearances; Juventus also went on to reach the 1995 UEFA Cup Final, only to be defeated by Parma. Despite his success, his inability to break into the starting line-up yet again led to his transfer to Fiorentina, where he apperead even less frequently than in previous seasons. He made only 7 appearances in Serie A with the Florentine club that season, and 1 more in the Coppa Italia, a trophy which Fiorentina would go on to win.