 Nyorai kuenderera mberi kweiyi ndima - Kutevera kuenda kwaCapello mushure mekukunda zita ra1995 96, pamwe nekukwegura uye kuenda pamudyandigere kwevamwe vatambi vakakosha, Milan yakatarisana nenguva dzerima munhoroondo yavo. Milan yakakundwa mu1996 Italian Supercup Final ne1995-96 Coppa Italia vakundi Fiorentina, uye 1996-97 uye 1997-98 mwaka zvaive zvisina kunaka, sezvo Milan yakatadza kukodzera kuEurope pazviitiko zvese izvi. Iyi mwaka isina zvibereko yakaona Milan ichiita shanduko dzinoverengeka dzevatungamiriri, kusanganisira Tabárez, uye kudzoka kusingabudirire kwaSacchi naCapello. Zvisinei, Costacurta, kuburikidza nehutungamiri hwake mukudzivirira, aizobatsira Milan kusvika ku1998 Coppa Italia Final, achirasikirwa neLazio. Nekuuya kwaAlberto Zaccheroni mumwaka wa19981999, Costacurta akaramba ari nhengo yakakosha yeiyo yekutanga line-up, uye akaonekwa muZaccheroni nyowani yevatatu-murume kudzivirira pamwe naMaldini naLuigi Sala. Costacurta akatumidzwawo zita rekuti mutevedzeri wemutungamiriri weMilan mwaka iwoyo, kumashure kwaMaldini, zvichitevera kuenda pamudyandigere kwaBaresi naTassotti. Pakupera kwemwaka, Milan yakakwanisa kutora yavo yegumi nematanhatu Scudetto kuhwina, uye Costacurta yechitanhatu yakazara, ichipedzisa pamberi peLazio nepfungwa imwe chete. Zvisinei, mwaka miviri yakatevera yaizoona Milan ichipfuura nemumwezve kusanaya mukombe. Milan yaizorasikirwa ne1999 Supercoppa Italiana kuParma, uye yaizopedza iri panzvimbo yechitatu muna 19992000, uye munzvimbo inoshungurudza yechitanhatu, kunze kwenzvimbo dzeChampions League, muna 2000-01. Milan yakatamburawo kubviswa kwekutanga mumutambo wekutanga uye wechipiri weChampions League mumwaka miviri iyoyo, uye Zaccheroni aizodzingwa pakati pe2000-01 mwaka, uye akatsiviwa naCesare Maldini semuchengeti wenguva pfupi. 