Education
In June 2009, Checchucci graduated from the Primavera team, and left for Lega Pro Prima Divisione (Italian 3rd highest level) side Lumezzane in co-ownership deal.
In June 2009, Checchucci graduated from the Primavera team, and left for Lega Pro Prima Divisione (Italian 3rd highest level) side Lumezzane in co-ownership deal.
Born in Bagno a Ripoli, the Province of Florence, Checchucci started his career at Fiorentina. In 2007-2008 season, he left for Prato, also located in Tuscany. In the next season, he left for Primavera under-20 team of Serie A side Chievo.
Lumezzane
On 24 June 2010, Checchucci along with Fabio Pisacane were bought back by Chievo.
But on 15 July 2010 he was re-signed by Lumezzane in another co-ownership deal. Crotone
In June 2011, Checcucci returned to Verona again.
However he left for F.C. Crotone in another co-ownership deal for €210,000. On 21 June 2013 Crotone acquired Checcucci outright for free.
Parma
Checcucci was sold to Parma in July 2013 for €200,000, however on 1 August 2013 Checcucci was signed by Slovenian club North Dakota Gorica in a temporary deal.
Savoia
In August 2014 Checcucci was signed by Savoia. AlbinoLeffe
On 5 August 2015 he was signed by AlbinoLeffe.