1999 was Capriati's best season in several years. She won her first title in six years at Strasbourg, defeating ninth ranked Nathalie Tauziat in a quarterfinal for her first win over a top 10 player in two years. She defeated Russian Elena Likhovtseva in the final. She won her second title of the year at Quebec City, defeating American Chanda Rubin in the final. She also reached the round of 16 at both Roland Garros and US Open. She finished the year at No. 23.  At the 2000 Australian Open, Capriati reached her first Grand Slam semifinal in nine years before losing to eventual champion Lindsay Davenport in straight sets.  At the Miami Masters, Capriati defeated World No. 6 Serena Williams for her first win over a player ranked in the top six in four years en route to a quarterfinal finish. Shortly after, Capriati was sidelined with right Achilles tendonitis in April and an elbow injury in June.  Capriati had a strong fall season, winning her ninth career title at Luxembourg, defeating Magdalena Maleeva. She also finished runner up in Quebec City to Chanda Rubin and was a semifinalist in Zurich. These results propelled Capriati back into the top 20 for the first time since April 1994. She qualified for the season-ending championships for the first time in seven years. Her year-end ranking was 14, her highest in seven years. Capriati was also a member of the US Fed Cup Team, winning a singles and doubles rubber in the US's victory over Spain in the final.

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