In July 2001, Di Masi joined Reggiana in co-ownership deal, as part of Adewale Wahab's deal to Roma. (50% registration rights of Di Masi tagged for 2,500 million lire; around €1,291,142, while Wahab tagged for 3,000 million lire; €1,549,371AS Roma SpA Report and Accounts on 30 June 2002 ) From November to February he was the first choice ahead of Patrick Bettoni; however, Bettoni was later restored as the club's first choice keeper. In the 2002–03 season, Di Masi was the backup of Raffaele Nuzzo and Luca Mondini. In January 2003, he left for Serie C1 side Pisa.
