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She then fell to María Vento-Kabchi in the first round of the China Open in Beijing and to Tamarine Tanasugarn in the second round of the Guangzhou International Women's Open.
In her final event of the year, she lost to world No.
Pennetta then lost in the first round of both the Cellular South Cup in Memphis, Tennessee and the Copa Colsanitas in Bogotá, Colombia.
These losses were followed by her first WTA Tour final at the Abierto Mexicano Telcel in Acapulco, where she was defeated by Iveta Benešová.
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.
At the Wismilak International in Bali, Pennetta lost in the second round to eventual quarterfinalist Gisela Dulko.She then lost in the first rounds of the Australian Open and the Open Gaz de France.In the next two weeks she won two titles in a row, the first one Copa Colsanitas defeating Lourdes Domínguez Lino in the finals 7–6(4), 6–4 and the second one in the Abierto Mexicano Telcel defeating Ľudmila Cervanová in three sets. The second rounds of the Pacific Life Open, the Qatar Total German Open and the Rome Masters.14, Ai Sugiyama, in the second round of the Zurich Open 6–7(1), 1–6.
In Pennetta's first event of the year, she reached the quarterfinals of the Brisbane International losing to Tatiana Golovin in three sets.
In July, she played yet another clay court tournament, where she was beaten in the final of the Internazionali Femminili di Palermo by Anabel Medina Garrigues.