Career
Born in Pietrasanta, the Province of Lucca, Massoni started his career at Lucca team Lucchese. He spent 2 seasons loaned to Viareggio in 2006-2007 and 2007-2008 season, winning Serie Doctorate and remain in Serie C2 by winning the relegation playoffs in 2008. After the bankrupt of Lucchese he was signed by Serie B team Sassuolo but farmed back to Viareggio in co-ownership deal, rejoining Lucchese team-mate Maikol Benassi and Luca Ruglioni.
He played 28 league matches that season and played both legs of promotion playoffs.
Despite the team finished as the losing semi-finalists, Viareggio promoted to fill the vacancies left by the bankrupted teams on 30 July. On 25 June Sassuolo bought him back but re-sold to Prima Divisione team Verona in another co-ownership deal, for €50,000 along with Sassuolo team-mate Filippo Pensalfini and Andy Selva.
He only played 6 times in the league and 1 more in the promotion playoffs. On 5 July 2010 Viareggio re-signed Massoni and also borrowed Davide Bertolucci from Verona.
He almost played all the matches for Viareggio, only missed 3 league matches due to suspensions.
In the cup he played 3 out of 6 possible matches. He started in the relegation playoffs, partnered with Lorenzo Fiale, winning Cosenza in aggregate. On 24 June 2011 Sassuolo bought Massoni back for a peppercorn of €500, in 2-year contract.
