Career
Born in Città di Castello, in the Province of Perugia, in Umbria region, Calderini was a youth product of A.C. (before Christ) Perugia. He played for both under-17 and U18 team in 2004-2005 season. After the bankruptcy of Perugia, he joined Serie B club Arezzo.
He spent 1½ seasons in the reserve team
In January 2007 he left for Serie C1 club Juve Stabia. Calderini left for Serie Doctorate club Flaminia in 2008.
He played 34 times for the Lazio club in the top division of amateur football (and fifth division of Italy until 2014). Frosinone
In July 2009 he was signed by fellow Lazio club Frosinone.
However he failed to secure a place in the Serie B club
On 31 August 2009 Calderini left for Lega Pro Prima Divisione (ex–Serie C1) club Foligno. Calderini and Guarracino were signed by Lega Pro Seconda Divisione (ex–Serie C2) club Sangiovannese on 12 July 2010. Frosinone relegated to L.P. Prime Division from Serie Bachelor in 2011.
Aprilia
On 26 August 2011 Calderini was sold to L.P. 2nd Division club Aprilia.
Cosenza
In July 2013 Calderini was signed by Cosenza. The club was among 6 additional teams that admitted to the fourth division from 2013-2014 Serie Doctorate to fill the vacancies on 5 August (originally 9, now 13 promoted plus 2 re-admission of relegated teams).
However at the end of season also saw the merger of the divisions of Lega Pro, as well as reduction of 69 teams to 60 teams (increased from 9 relegated teams to 18 teams). Cosenza mathematically promoted to Serie C after the round 30 matches.
That seasob Calderini scored 7 goals as team joint-second topscorer, along with Manolo Mosciaro behind Gianluca De Angelis (11 goals) and ahead Jonatan Alessandro (5 goals).