Bertolini began his career on satellite tournaments and the ATP Challenger Tour, where he was the first win of twelve career titles in doubles in 1998. In 1998, he stood next to Devin Bowen also in the doubles final of the ATP tournament in Santiago; However, the match went into three fought sets, each of which was decided in the tie-break, lost. The following year, he reached the final of the International Series Gold tournament in Barcelona, which he lost at the side of Cristian Brandi vs. Paul Haarhuis and Yevgeny Kafelnikov. After three more final defeats at the ATP World Tour, he was on the side of Simon Aspelin in 2003 two doubles titles, and therefore the greatest successes of his career win. The highest quotation in the tennis world ranking he reached in 1995 with position 329 in single and in 2004 with position 36 in doubles.
In the individual he was never able to qualify for a Grand Slam tournament. In the doubles competition, he reached the quarterfinals of the U.S. Open in 2001 and the quarterfinals of the French Open 2003. Mixed In each case he was once at Wimbledon and at the French Open in the first round.
Bertolini played between 2002 and 2004 six double appearances for the Italian Davis Cup team. His record on the first page of Giorgio Galimberti and later Andreas Seppi was positive at 4:2.