Rubuta ci gaba don wannan sakin layi - A karkashin mulkin Ancelotti, Milan ta kuma lashe gasar Supercoppa Italiana ta 2004
, kuma sun kasance masu tseren baya-baya na Serie A zuwa Juventus a cikin 2004-05 da 2005-06 (duka "Scudetti" daga baya an goge su 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 hannun 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.