 Nyorai kuenderera mberi kweiyi ndima - Milan yakasvika kumagumo e1989-90 Coppa Italia, ichirasikirwa neJuventus. Milan yakakwanisawo kutora mazita eEuropean Super Cup akatevedzana muna 1989 na1990, pamwe chete nemazita eIntercontinental Cup akatevedzana, zvakare muna 1989 na1990. Mwaka wakatevera, mumwaka wekupedzisira waSacchi nekirabhu, Milan yakadzingwa mumakwikwi ekupedzisira eEuropean Cup nevakapedzisa Marseille, uye vakapedza wechipiri muSerie A, kuseri kweSampdoria, zvakare nekudzivirira kwakanakisa muligi, vachibvuma zvibodzwa gumi nemapfumbamwe chete. Milan yakasvika kumasemi-fainari eCoppa Italia, ichirasikirwa nemakwikwi eRoma. Muna 1989, Maldini akapihwa mubairo weBravo, semutambi akanakisa ari pasi pemakore makumi maviri nematatu mumakwikwi eEuropean. 