Weah joined A.C. 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.
Van Basten had been hopeful of playing for his country at the 1994 World Cup as well as for his club in the 1994–95 season after spending the whole 1993–94 season out of action (missing Milan's victory in the European Cup as well as their Serie A title glory), but his club ordered him not to take part in the World Cup amid fear of ruining his rehabilitation. Father Joop (1931-2014) proudly declared before he died that he had no regrets whatsoever of his son's shortened career because "Marco became a top, top player and fulfilled all my hopes and dreams". Joop himself was a semi professional in Holland in the 1950's but attended his son's every game at Ajax and Milan. Marco finally conceded defeat in his battle to recover on 17 August 1995, when he announced his retirement as a player after two whole years on sidelines.Van Basten made a farewell appearance to thank the Milan fans before a home game at the San Siro, with an emotional Milan coach Fabio Capello breaking down in tears.