Born in Rovereto, Trentino, Calliari started his career in the same province, for Mori–St.Stefano. In 2002, he was signed by Serie A side Chievo[2] and spent 6 seasons at their youth teams.
Calliari was in Chievo's Primavera under-20 team in 2007–08 season.[3]
He graduated from the youth team in June and loaned to Italian Lega Pro 1st Division (3rd highest level) club Lumezzane along with first team member Tommaso Chiecchi in July 2008.[4]
On 26 June 2009, Calliari (for €325,000[5]) along with ex-Primavera teammate Nicolò Brighenti (€425,000) were sold to Serie B side Triestina in co-ownership deals .[6][7] Co-currently, Chievo signed Dario D'Ambrosio (€340,000)[8] and Marcello Cottafava (€420,000[5]) in co-ownership deals. On 9 July 2009, Chievo loaned D'Ambrosio and Cottafava back to Triestina, and Calliari and Brighenti were loaned to Lumezzane[9] and Pergocrema[10] of Italian Lega Pro 1st Division respectively.
After Triestina re-admitted to Serie B in August 2010, Triestina bought back Cottafava for €210,000[5] and Chievo bought Calliari back for €220,000[5] (while D'Ambrosio and Brighenti already back to their original club in January 2010). He was loaned to Lumezzane for a third time on 6 August 2010.[11] It is because Calliari's contract had a nominal accounting value of €440,000 (purely through player swap), which Chievo chose to amortize it proportionally to contract length, instead of immediately write-down the inflated residual value. However, Chievo had write-down €506,695 for the sale of Brighenti in June 2011.
On 31 August 2011 he joined South Tyrol, the team form his home autonomous region Trentino – South Tyrol.
On 22 August 2012 Calliari was sold to Monza in a co-ownership deal for just €500; Chievo also write-down the residual value of €114,000.[12][13] On 20 February 2014 he was released.[14]
In October 2014 he was signed by Mori St.Stefano.[15]