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She debuted in the main draws of all four Grand Slam tournaments.

Her best result was the third round of the Roland Garros, where she defeated 21st-seeded American Lisa Raymond in the second round, before losing to Hungary's Petra Mandula.

At the Budapest Grand Prix, Pennetta lost in the semifinals to eventual champion Jelena Janković in straight sets. 6, Nadia Petrova, in the second round of the Internazionali BNL d'Italia in Rome before falling to world No. At the French Open, Pennetta lost in the first round, once more to Smashnova in straight sets.

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In 2003, Pennetta lost in the semifinals of the Hyderabad Open to eventual champion Tamarine Tanasugarn.

She also reached the quarterfinals at the Canberra Women's Classic, Copa Colsanitas, and Abierto Mexicano Telcel.

Pennetta won ten other WTA singles titles, including the 2014 Indian Wells Masters, in which she defeated the top two seeds, both of whom were ranked in the top 3.

She also was a mainstay in the Fed Cup team competition, helping to win four titles for Italy in 2006, 2009, 2010, and 2013.

Pennetta started the year at the Tier V Canberra Women's Classic, where she lost in the quarterfinals to Julia Vakulenko.

At the Australian Open, she lost in the first round to Italian Antonella Serra Zanetti in straight sets.

The following year, she lost in the second round of her first qualifying tournament for a WTA Tour main draw, the Internazionali Femminili di Palermo.

In 1999, Pennetta won two singles titles and two doubles titles on the ITF circuit.

She played her first main draw WTA Tour match at the Cellular South Cup in 2002, when she lost in the first round.

She also lost in the first round in Palermo, but reached the second round of the Idea Prokom Open in Sopot.

She played both of the Tier I springtime hard-court tournaments in the United States.

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