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.[1] In June 2008 Pescara made a discount on both players, which both were sold for €450,000.[2]
He made his Serie A debut on 27 April 2008 in a 0–0 home tie against Atalanta.[3]
Di Matteo was confirmed as part of the Palermo first team squad for the 2008–09 season, but was never featured on the patch and he was successively loaned out to Serie B outfit Cittadella on February 2, 2009 for the remainder of the season.
He spent the first half of the 2009–10 season on loan to Crotone.[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.[5] In return Nicola Rigoni was sold back to Vicenza also for €200,000.[5] After failing to make a single appearance with Palermo, he was loaned out to Lecce on 31 January 2012.[7] He then returned to Vicenza in August 2012 after being deemed as surplus to requirements from Palermo, and played one season in Serie B and the first half of the 2013–14 season in the Lega Pro Prima Divisione.
In January 2014, he left Vicenza for Serie B club Padova, amassing only a total eight appearances for the club, and suffering a second consecutive relegation. He successively found himself without a club after Padova was excluded from the Italian league system due to financial issues.
On 12 July 2019 he returned to Teramo, signing a 2-year contract.[8]
