Career
A player of wide range, he could appear as a midfielder or a defender, always on the right flank. A product of Brescia Calcio"s youth system, Diana made his debuts for the first team in Serie Bachelor in 1997, and played his first Serie A game on 31 August of the same year, against Inter Milan. He played one season with Hellas Verona F.C. in a co-ownership deal, helping the side to a final ninth position in the top level, and left for A.C. (before Christ) in 2001.
Diana was used irregularly by the Emilia-Romagna side, winning the Italian Cup in his first season, but hardly featuring at all in 2002-2003.
In January 2003 he moved on loan to Reggina Calcio along with Emiliano Bonazzoli, posteriorly signing for University College Sampdoria at the end of the campaign. In the 2006 summer, Diana signed for United States. Città di Palermo for €5 million, with Sampdoria also selling Marco Pisano to the same club for €4 million and receiving Massimo Bonanni (50% for €2million), Pietro Accardi (€2 million) and Christian Terlizzi (50% for €15 million).
On 30 January of the following year he was sold to Torino F.C. in a permanent move, for €1.2 million. In early January 2010, Ultras of Torino attacked club players during David Di Michele"s birthday party.
After the incident, Riccardo Colombo, Diana, Di Michele, Massimo Loviso, Marco Pisano, Francesco Pratali and Paolo Zanetti were transferred to other clubs, with only Rolando Bianchi, Angelo Ogbonna and Matteo Rubin remaining.
Diana joined Air Corps Bellinzona in Switzerland on loan in early February 2010, making his Super League debut on the 21st in a 1–2 away loss against Football Club Luzern, eventually contributing solidly (15 matches, 14 starts) as the club narrowly retained its division status. Subsequently, 32-year-old Diana returned to Torino. On 4 January 2011 he mutually terminated his contract, re-signing for Bellinzona (on a permanent basis) the following day.
After impressing for Sampdoria, Diana received his first call-ups to the Italian national team, making his debut in a friendly match with Spain on 28 April 2004.