 Ramba uchinyora ndima iyi - Milan yakavazve simba guru muItaly uye muEurope pasi paCarlo Ancelotti. Mumwaka wa2001-02, Milan yakapedza iri pachinzvimbo chechina, ichikwikwidza kuenda kuChampions League, uye zvakare yakasvika kumagumo avo akanakisa muEFAFA Cup, vachirasikirwa mumasemifainari. Muna 2002, Maldini akapihwa iyo Premio Nazionale Carriera Esemplare Gaetano Scirea, nekuda kwebasa rake uye hunhu. Mwaka wakatevera, Maldini akabatana naAlessandro Nesta, Alessandro Costacurta naCafu, avo, pamwe naJaap Stam mumwaka wa2004-05, vakaumba mutsara unotyisa wekuzvidzivirira muItari neEurope. Milan yakapedza iri yechitatu muSerie A, asi Maldini akakunda Coppa Italia yokutanga yebasa rake, achikunda Roma mumutambo wokupedzisira. Musi wa15 Kurume 2003, akaita mutambo wake wechi500 muSerie A. 