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|Date of birth||26 July 1983|
|Place of birth||Brindisi, Italy|
|Height||1.78 m (5 ft 10 in)|
|2003–2004||→ Como (loan)||7||(0)|
|2004–2005||→ Salernitana (loan)||6||(0)|
|2005||→ Ancona (loan)||16||(0)|
|2005–2006||→ Triestina (loan)||1||(0)|
|2006||→ Olbia (loan)||6||(0)|
|2006–2007||→ Pavia (loan)||22||(2)|
|2007–2008||→ Varese (loan)||0||(0)|
* Senior club appearances and goals counted for the domestic league only.
Born in Brindisi, southern Italy, Massaro started his professional career at AC Fiorentina of Florence. He played his only match at Serie A on 10 June 2001. After the bankrupt of La Viola, he joined Parma AC in August 2002. In summer 2003 he was included in a 6-men swap, which Massaro (for €2M), Filippo Porcari and Luca Ferretti of Parma swap for Davide Favaro, Marco Donadel (for €2M), 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 another €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 a free transfer.
- Parma F.C. S.p.A. bilancio (financila report and accounts) on 30 June 2007 (in Italian), PDF purchased from Italian C.C.I.A.A.
- "AC Milan Group 2007 Annual Report". AC Milan (in Italian). Archived from the original (pdf) on 25 April 2011.
- "UFFICIALE: Roberto Massaro al Varese". Tutto Mercato Web (in Italian). 3 August 2007. Retrieved 11 June 2011.
- "UFFICIALE: Olbia, preso Massaro". Tutto Mercato Web (in Italian). 31 January 2008. Retrieved 11 June 2011.