Career
Born in Sondrio, Lombardy, D'Alessandro started his career at Calcio Como. On 31 August 2006 he was signed by Genoa C.F.C. In 2009 he was signed by Reggiana in temporary deal.
In July 2010, the loan was extended to another season. On 31 January 2011, Reggiana bought him in co-ownership deal for a peppercorn of €500. On 31 August 2011 Reggina bought D'Alessandro from Reggiana for €100,000, with Genoa retained 50% registration rights.
In June 2013 Genoa gave up the remain 50% registration rights to Reggina. On 2 September 2013 D'Alessandro left for Lega Pro Seconda Divisione club Cuneo. After the club relegated, he joined Serie C club Monza.
In January 2015 he joined Serie B club Pro Vercelli as a free agent. He took no.2 shirt from Andrea Marconi.