Career
Born in Brindisi, southern Italy, Massaro started his professional career at Air Corps Fiorentina of Florence. He played his only match at Serie A on 10 June 2001. After the bankrupt of Louisiana Viola, he joined Parma Air Corps in August 2002.
In summer 2003 he was included in a 6-men swap, which Massaro (valued €2M), Filippo Porcari and Luca Ferretti of Parma swap for Davide Favaro, Marco Donadel, and Mirko Stefani of Milan, all in co-ownership deal.
He then spent 4 seasons on loan to clubs in Serie B, Serie C1 and Serie C2. In June 2007, Milan got full registration rights for €90,000, but Massaro then transferred to Varese.
Since January 2008 he played for Olbia, but just played once. In June 2008 Olbia signed him on free transfer.
