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Following this loss, Capriati decided to take a break from tennis. Capriati, unranked, played her first match in 15 months in Essen, where she reached the quarterfinals, losing to Jana Novotná in three sets.She reached her first final in more than three years at Chicago, defeating Monica Seles en route, before losing again to Novotná in three sets.She finished her first season as a professional at World No. Throughout the season Capriati set multiple "youngest ever" records.
Capriati became the youngest person to ever reach the semifinal round of the tournament, losing to Sabatini.
At the US Open, Capriati defeated Sabatini in the quarters but lost in the semis to eventual champion Seles after serving for the match twice. Capriati also won the only doubles title of her career at the Italian Open, partnering with Seles.
She was also the fourth-youngest player to win a WTA title.
In her second season as a touring pro, Capriati established herself as a consistent top-10 player.
Capriati next defended her title in San Diego, defeating Conchita Martínez in the final, the only time that Capriati won back-to-back singles titles during her career.