 Sezvo Cassano akatarisana nemakwikwi enzvimbo muMilan kutanga XI kubva kune vanofarira Zlatan Ibrahimović, Alexandre Pato naRobinho, kufungidzira kwakawanda kwakaumbwa pamusoro penguva yake yemberi yemwaka unotevera, sezvo Cassano aida kuwana nguva yakawanda yekutamba, nekuda kwechido chake chekuchengetedza nzvimbo yake muItaly National side. Kunyange zvazvo pakutanga akanga akabatanidzwa kune mamwe makirabhu, akagara naMilan, uye mushure mekugadzirira kwakanaka kwemwaka, akakunda 2011 Supercoppa ItaliananeMilan pamusoro peInter, uye akarova mumutambo wekutanga weSerie A wemwaka wa2011-12 vachipesana neLazio. Musi wa 29 Gumiguru 2011, zvichitevera mutambo weMilan uchipesana neRoma muRome, Cassano akaiswa muchipatara mushure mekurwara sitiroko paakasvika kuMilan, uye akavhiyiwa musi wa 4 Mbudzi. Akadzokera kuchikwata chekutanga musi wa 7 Kubvumbi 2012, mushure memwedzi ingangoita mitanhatu ari padivi-mitsara, achiratidza semunhu anotsiva mukukunda kweMilan 2 1 kumba kuFiorentina muSerie A, uye akagamuchira kurumbidzwa kubva kune vateereri paakapinda mumunda weGianluca Zambrotta muminiti ye79. Akaonekwawo sechinotsiva mukukunda 10 kumba vachipesana neGenoa musi wa25 Kubvumbi, uye musi wa29 Kubvumbi, akarova chibodzwa chake chekutanga kubva pakuvhiyiwa kwake, mukukunda 41 pamusoro peSiena, achigadzirawo zvibodzwa zviviri zvaIbrahimović panguva yemutambo. Milan yakapedza mwaka weSerie A iri panzvimbo yechipiri kuseri kweJuventus, ichisvikawo kuma semi fainari eCoppa Italia, uye kuma quarter fainari eChampions League. 