 Nyorera kupfuurira kweiyi ndima - PaAC Milan, Šimić akabva angogadzirwa nhengo yechikwata chekutanga pasi paCarlo Ancelotti, uyo akachinja nzvimbo yaŠimić yekutamba kubva pakati kusvika kurudyi kumashure mumutsara wevarume vana vanodzivirira. Kutanga kwake kwe AC Milan kwakauya mumutambo we 2002-03 Champions League wechitatu wekutsvaga mutambo we Slovan Liberec musi wa 28 Nyamavhuvhu 2002. Šimić akaenderera mberi nekuita 12 kuoneka kwe AC Milan mukumhanya kwavo kuenda kuEFAFA Champions League zita muna 2003, kunyangwe akasiiwa kubva kumativi ese maviri ekupedzisira kurwisa Inter uye mutambo wekupedzisira.vachipesana nevanokwikwidzana navo veSerie A Juventus paOld Trafford. Akaita 29 Serie A kuonekwa kwe AC Milan mumwaka wake wekutanga nekirabhu, asi mumwaka mitatu inotevera haana kuzombodzora nzvimbo yake sechikwata chekutanga nguva dzose, achingoita 27 ligi kuoneka mumwaka mitatu. Muna Chivabvu 2006, akasaina chibvumirano chekuwedzera kusvika muna 2009 ne AC Milan, masvondo mashoma mushure mekushora pachena murairidzi Carlo Ancelotti nekuda kwekushaikwa kwenguva yekutamba. 