With Milan, Costacurta won the "Scudetto" seven times and the European Cup/UEFA Champions League five times, in 1989, 1990, 1994, 2003 and 2007, although he did not feature in the squad for the 1994 and 2007 finals. Costacurta also won a Coppa Italia, five Supercoppa Italiana, four UEFA Supercups and two Intercontinental Cups with Milan. He also managed to reach three more UEFA Champions League finals, wherein Milan lost to Marseille in 1992–93, Ajax in 1994–95 and Liverpool in the 2004–05, with a total of eight finals reached and five won. He also reached two more consecutive Intercontinental Cup finals, where Milan were defeated 3–2 by São Paulo in 1993 and 2–0 by Vélez Sársfield (where Costacurta was sent off in the 85th minute) in 1994, as well as losing out on the 1993 UEFA Super Cup to Parma under Fabio Capello, and the 2003 Intercontinental Cup to Boca Juniors under Carlo Ancelotti. Costacurta made 662 appearances for Milan throughout his career (458 in Serie A, 78 in the Coppa Italia, 108 in European Competitions, 5 appearances in the Intercontinental Cup final, 6 in the Italian Super Cup final, and 7 in the UEFA Super Cup final). He only scored three goals in Serie A, with his first coming in a 3–1 defeat in the Milan–Inter derby on 13 March 1990. The second came in a 4–1 over Roma at the San Siro, on 3 November, where he scored the fourth goal of the match, and his final goal was scored in a 3–2 defeat to Udinese on the final match of his career. Costacurta is the third highest appearances holder for Milan in official matches, with 662 caps; only Franco Baresi (719) and Paolo Maldini (902) have managed more appearances.