Nyorai kuenderera mberi kweiyi ndima - Pasi pehutongi hwaAncelotti, Milan yakakundawo 2004 Supercoppa Italiana
, uye vakangawo back-to-musana Serie A runners-up kuna Juventus muna 2004-05 uye 2005-06 (zvose "Scudetti" vakanga gare gare vadzimwa kubva zvinyorwa mabhuku Juventus nokuda kubatanidzwa kirabhu wacho "Calciopoli" nhema). Mumwaka wa2004-05, Ancelotti akatungamirawo Milan kuenda kumakwikwi ekupedzisira eChampions League muna2005, uko vakarasikirwa neLiverpool 2-3 pakurohwa mushure mekunge vatamba 3-3 munguva yakajairika. MuCoppa Italia, chikwata chacho chakakundikana kupfuurira kusvika kumakota ekupedzisira. Mwaka wakatevera, Milan yakatarisana zvakare nekushungurudzika sezvo vakarasikirwa neBarcelona mumasemifainari eChampions League, uye vakangosvika kumaquarterfainari eCoppa Italia.