Massu was introduced to tennis at age five by his grandfather, from age 12, he was trained at the Valle Dorado tennis academy.
Massu has a style characteristic of a clay court specialist, with strong baseline play characterized by a solid forehand and backhand. Massu is known for his fighting spirit, especially when playing for Chile, as he has demonstrated at the 2004 Olympics and at numerous Davis Cup matches. He has also turned around difficult matches.
In August 1998, Massu won his first future tournament, in Spain. The following month he claimed his first challenger event, in Ecuador. He won his second challenger tournament in June 1999, in Italy. In September 1999, he successfully defended his title in Ecuador. In November 1999, he won the Santiago challenger event, and cracked the top 100 in singles for the first time.
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