Career
Piacenza
Calderoni made his first team debut on 25 May 2008 against Cesena, the 2nd last match of the season. On February 2010, Piacenza and Serie A outfit Palermo agreed for a loan exchange between Calderoni and Romanian full-back Cristian Melinte, with the former joining the rosanero with immediate effect. He returned at Piacenza at the end of the season, with only one appearance during his short stint with the Sicilian side.
In January 2011 is made official his transfer on loan Ascoli.
Grosseto
In January 2012 Calderoni was signed by Grosseto. Bari
On 14 August 2013, Calderoni was signed by Chievo.
Half of the registration rights, valued for €90,000, was immediately swap with the full registration rights of Claiton dos Santos, valued for undisclosed fee. Calderoni signed a 5-year contract with Bari.
In June 2015 Cheivo bought back Calderoni.
Chievo
Calderoni re-joined Chievo on 25 June 2015. On 13 July he was signed by United States. Latina Calcio in a temporary deal. He was selected to 2009 Mediterranean Games and 2009 Fédération internationale de football association U-20 World Cup along with team-mate Francesco Bini.