Kammala wannan jumla: A karkashin mulkin Ancelotti, Milan ta kuma lashe gasar
2004 Supercoppa Italiana, kuma sun kasance masu tsere na Serie A na baya zuwa Juventus a 2004-05 da 2005-06 (duk "Scudetti" an share su daga baya daga littattafan tarihin Juventus saboda shigar da kulob din cikin "Calciopoli" abin kunya). A lokacin kakar wasa ta 2004/05, Ancelotti ya kuma jagoranci Milan zuwa wasan karshe na gasar zakarun Turai ta 2005, inda suka yi rashin nasara a kan Liverpool 2-3 a bugun fanareti bayan an tashi 3-3 a cikin lokaci na yau da kullun. A cikin Coppa Italia, ƙungiyar ba ta iya wuce wasan kusa da na karshe ba. A kakar wasa ta gaba, Milan ta sake fuskantar takaici yayin da suka yi rashin nasara a kan Barcelona a wasan kusa da na karshe na gasar zakarun Turai, kuma sun kai wasan kusa da na kusa da na karshe na Coppa Italia.