His best results of the year were losing in the Peru F3 semi finals to Luis Horna and the quarter-finals of the Resistencia to Guillermo Coria.

In 1999, Massa won his first Futures tournaments in Buenos Aires defeated Martín Vassallo Argüello and Asunción over Leonardo Olguín.

The 2001 season started slowly for Massa, but in September he won two consecutive Challengers in Florianópolis and São Paulo defeating Gastón Etlis and Martín Vassallo Argüello respectively, before losing to Agustín Calleri in Guadalajara in the following week and Marcelo Ríos in Santiago.

Massa had a poor 2002 and returned to playing Futures events in late 2003 where he won two tournaments defeating Carlos Berlocq in Chile and Diego Hartfield in Uruguay.

Massa's last Challenger tournament win was in 2005 in La Serena over Mariano Puerta who would go on to make the Roland Garros final in that season.