Ku qor sii socodka faqradan - Mudadii Ancelotti uu xukumayay, Milan waxay sidoo kale ku guuleysatay 2004 Supercoppa Italiana
, sidoo kale waxay ahaayeen kuwa ku soo laabtay Serie A runners-up ee Juventus 2004/05 iyo 2005/06 (labadaba "Scudetti" ayaa markii dambe laga tirtiray buugaagta rikoodhka ee Juventus sababtoo ah ku lug lahaanshaha naadiga "Calciopoli" fadeexad). Intii lagu jiray xilli ciyaareedkii 2004-05, Ancelotti wuxuu sidoo kale Milan u horseeday finalka Champions League 2005, halkaas oo ay Liverpool kaga badiyeen 2-3 gool oo ciqaab ah ka dib markii ay barbaro 3-3 ah ku gaareen waqtiga caadiga ah. Koobka Talyaaniga, kooxdu ma awoodin inay ka gudubto wareega afar dhamaadka. Xilli ciyaareedkii xigay, Milan ayaa mar kale la kulantay niyad jab markii ay ka badiyeen Barcelona semi-finalka Champions League, waxayna kaliya gaareen afar dhamaadka Coppa Italia.