In his period at Bologna, Di Vaio regained reputation as a key prolific striker, rapidly becoming a fan favourite, as well as team captain and one of the reference players during the two club takeovers in the 2010–11 season, ensuring himself a contract extension until June 2013; following the announcement, Di Vaio also state his desire to spend the rest of his footballing career as a Bologna player. However, on 4 May 2012, Di Vaio confirmed that the 2011–12 season will be his last with Bologna, and that he would be considering various options for his future.