Born in Milan, Gobbi started his senior career in fourth-tier Serie C2 club Pro Sesto in 1998.
[3] (but made Viola received an extra cost saving of €200,000)[4] He scored his first goal for the Fiorentina against Juventus on 1 March 2007.
[6] Initially deployed in his natural role as a central midfielder, Gobbi's first season at the club saw him become a regular as a left-back from December 2010 onwards as a consequence of Luca Antonelli's January 2011 departure.
[11] Immediately after joining Fiorentina, Gobbi was called up for the Italy national football team by manager Roberto Donadoni.
[12] He made his senior national team debut in a 2–0 friendly defeat against Croatia in Livorno, on 16 August 2006, coming on as a substitute for Massimo Ambrosini in the 75th minute.