Weah joined AC Milan in 1995, with whom he immediately won the Italian league in 1996 under Fabio Capello, playing alongside Roberto Baggio and Dejan Savićević in Milan's attack, as well as Marco Simone, on occasion, and finishing the season as Milan's top goalscorer; he won the Serie A title once again in 1999. During his time with the club, he also reached the 1998 Coppa Italia final, and finished as runner-up in the Supercoppa Italiana on two occasions, in 1996 and 1999. Despite their European dominance in the early 1990s, Milan were less successful in Europe during this time, however, with their best result being a quarter-final finish in the 1995–96 UEFA Cup.