He won a Futures doubles title in Santiago de Chile and reached three finals in Argentina, Uruguay and Slovenia.

2005 : He reached his first career Challenger Singles final in Buenos Aires and in Doubles in Nashville (USA).

He played his first Gran Slam in Roland Garros as a qualifier and entered the main draw, but lost vs. world No.

2007 : He reached the final of the São Paulo Challenger and advanced to his first ATP SF in his hometown of Buenos Aires.

2009 : During a practice at the Copa Petrobras Challenger in Buenos Aires, Diego twisted his knee and tore its ligaments.