Ди Дженнаро
On 27 June 2009, Milan reclaimed Di Gennaro from the co-ownership with Genoa via a blind auction, after the two teams had failed to reach an agreement, for €1.25 million. Di Gennaro signed a new 3-year deal. However, during a pre-season friendly he suffered a broken metatarsal, which forced him out for the first months of the season. After recovering from the injury, he struggled to return to form, playing only two Coppa Italia games. To get some more playing time, on 29 January 2010 he was loaned to Livorno for the remainder of the season.