 Nyorai kuenderera mberi kweiyi ndima - Kutevera kuenda kwaCapello, uye kuchembera uye kuenda pamudyandigere kwevatambi vakati wandei, Milan yakatambura mhedzisiro inoshungurudza mumwaka mishoma inotevera, ichiita shanduko dzinoverengeka dzevatungamiriri. Milan yakarasikirwa neSupercoppa Italiana kuFiorentina muna 1996, uye yakatadza kukwanisa kukwikwidza kumakwikwi eEuropean kwemwaka miviri yakateedzana, pamwe nekutambura kubviswa muchikamu cheboka mu1996 97 Champions League. Zvichitevera Franco Baresi uye Mauro Tassottis retirement mushure megore ra1996-97, Maldini akagadzwa kuve kaputeni weMilan. Pasinei nematambudziko akasangana neMilan panguva iyi, kuburikidza nehutungamiriri hwaMaldini, vakasvika kumagumo eCoppa Italia muna 1998, vachirasikirwa neLazio, uye vakahwina mukombe weSerie A wa1998-1999 pasi paAlberto Zaccheroni, vachipedza poindi imwe pamberi peLazio. Akaita 400th yake Serie A kuoneka musi wa25 Kubvumbi 1999. Mumwaka wa1999 kusvika 2000, Milan yakarasikirwa neSupercoppa Italiana vachipesana neParma, vakapedza vechitatu muSerie Auye vakapedza vari pasi peboka ravo reChampions League. Milan yakabviswa muchikamu chechipiri cheChampions League mwaka unotevera uye yakapedza iri pachinhanho chechitanhatu muSerie A, ichitadza kupinda muChampions League, uye yakatora chikamu muEFAFA Cup mwaka unotevera. 