[1][2] After the bankrupt of Lucchese he was signed by Serie B team Sassuolo but farmed back to Viareggio in co-ownership deal, rejoining Lucchese teammate Maikol Benassi[3] and Luca Ruglioni.
On 25 June Sassuolo bought him back but re-sold to Prima Divisione team Verona in another co-ownership deal, for €50,000[6][7] along with Sassuolo teammate Filippo Pensalfini and Andy Selva.
[8] On 12 July 2010 Viareggio re-signed Massoni and also borrowed Davide Bertolucci from Verona.
[13][14][15] He started in the relegation playoffs, partnered with Lorenzo Fiale, winning Cosenza in aggregate.
[16][17] On 24 June 2011 Sassuolo bought Massoni back for a peppercorn of €500, in 2-year contract.