Diego Milito
On 21 August 2008 it was confirmed that Di Vaio had signed for Serie A side Bologna FC, recently promoted from Serie B. This reunited with former Genoa teammate Adaílton. Di Vaio was a surprise star in the 2008–09 season, scoring an impressive 24 goals for a mediocre Bologna side. He finished the season as joint second top-scorer alongside Genoa C.F.C. striker Diego Milito. At the end of season Bologna signed him on free transfer.