Di Matteo started his career with Pescara, establishing himself as a player with good potential despite his young age.

On January 31, 2008 Palermo signed Di Matteo from then Serie C1 club Pescara, together with teammate Edgar Çani in co-ownership deal for €500,000 and €600,000 respectively.

[4] In February 2010, Di Matteo agreed to leave Crotone and join Vicenza, this time in a co-ownership bid between Palermo and his new club, for a peppercorn fee of €500.

[5][6] Di Matteo made his second comeback to Palermo in June 2011, as his co-ownership was solved in favour of the rosanero for €200,000.

He successively found himself without a club after Padova was excluded from the Italian league system due to financial issues.