Donadoni briefly rejoined Milan after the 1997 MLS season, helping lead them to another Coppa Italia final in 1998 during Fabio Capello's second spell with the club. He also won another Serie A title under Alberto Zaccheroni in 1999, his sixth and final career Serie A title. In total, Donadoni scored 18 career Serie A goals for Milan in 287 appearances, and 23 in 390 appearances throughout all competitions.