Kammala jumla mai zuwa: A ranar 11 ga Yuli 2010, an sanar da cewa Matteo Darmian zai shiga sansanin horar da Palermo a Austria, bayan da Milan da kungiyar Serie A ta Sicily suka amince da ka'idar game da canja wurin da ya shafe shi. Motsawar, wanda aka bayyana a matsayin tayin haɗin gwiwa, an sanar da shi a hukumance ta Palermo a rana mai zuwa. Kudin da aka biya shi ne € 800,000. Darmian ya fara bugawa "Rosanero" a ranar 16 ga Satumba, 2010, a wasan Europa League da Sparta Prague, wanda kuma ya sa ya fara bugawa a gasar Turai. Farkon wasansa a Palermo ya kasance a wasan wasa na huɗu na kakar wasa ta bana, yana fitowa Javier Pastore a wasan da suka ci Juventus da 3-1. A ranar 6 ga Fabrairun 2011, ya buga wasansa na farko a matsayin mai farawa a gasar a nasarar 4 zuwa 2 ga Palermo a Lecce, amma an sauya shi a minti na 33 saboda rauni. Ya kammala kakar wasa tare da wasanni 16 a tsakanin
Serie A, Europa League da kuma Coppa Italia.