 Casolla started his senior career at amateur (non fully professional) club Riccione, a minor team in the Province of Rimini in 2010–11 Serie D. In the next season the club moved to Rimini and renamed as Real Rimini, also in the fifth division.Casolla was a member of Serie D representative team that season.On 30 August 2011 Casolla returned to Cesena but immediately left for San Marino Calcio in temporary deal with option to sign half of the registration rights.