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She was unsuccessful in her several attempts to qualify for WTA Tour main draws in 2000.The following year, she limited her play to the ITF circuit.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 both of the Tier I springtime hard-court tournaments in the United States.She beat Ľudmila Cervanová in the first round of the Pacific Life Open in Indian Wells before losing to Maria Sharapova.
She became Italy's first top-ten female singles player on 17 August 2009 and the first Italian to be ranked world No. She became a Grand Slam singles champion, winning the US Open in 2015 by defeating her childhood friend Roberta Vinci in the first all-Italian Grand Slam final.
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.
In the first grass-court tournament of her career, she defeated Marion Bartoli in the first round of the DFS Classic in Birmingham, before losing to world No. Pennetta achieved the same result at the Ordina Open, falling to world No. At Wimbledon, she was beaten by Petrova in the first round in three sets.
The following week at the clay court Orange Prokom Open in Sopot, Poland, Pennetta won her first WTA Tour title, defeating Klára Koukalová in the final. 1, Lindsay Davenport, in the quarterfinals of the Western & Southern Financial Group Women's Open in Cincinnati and to world No.
25, Magdalena Maleeva, in the first round of the US Open, 6–2, 4–6, 4–6.
She played her first main draw WTA Tour match at the Cellular South Cup in 2002, when she lost in the first round.