Anna Kournikova practices her backhand for a match at the Family Circle Cup Tennis Tournament on Daniel Island in Charleston, South Carolina, where hundreds of Charleston Air Force Base (AFB) personnel volunteer to provide security.
In 1998, Kournikova broke into the WTA's top 20 rankings for the first time, when she was ranked No. 16. At the 1998 Australian Open, Kournikova lost in the third round to World No. 1 player Martina Hingis. She also partnered with Larisa Neiland in women's doubles, and they lost to eventual champions Hingis and Mirjana Lučić in the second round. Although she lost in the second round of the Paris Open to Anke Huber in singles, Kournikova reached her second doubles WTA Tour final, partnering with Larisa Neiland. They lost to Sabine Appelmans and Miriam Oremans. Kournikova and Neiland reached their second consecutive final at the Linz Open, losing to Alexandra Fusai and Nathalie Tauziat. At the Miami Open, Kournikova reached her first WTA Tour singles final, before losing to Venus Williams in the final.
Kournikova then reached two consecutive quarterfinals, at Amelia Island and the Italian Open, losing respectively to Lindsay Davenport and Martina Hingis. At the German Open, she reached the semifinals in both singles and doubles, partnering with Larisa Neiland. At the 1998 French Open Kournikova had her best result at this tournament, making it to the fourth round before losing to Jana Novotná. She also reached her first Grand Slam doubles semifinals, losing with Neiland to Lindsay Davenport and Natasha Zvereva. During her quarterfinals match at the grass-court Eastbourne Open versus Steffi Graf, Kournikova injured her thumb, which would eventually force her to withdraw from the 1998 Wimbledon Championships.[8] However, she won that match, but then withdraw from her semifinals match against Arantxa Sánchez Vicario.[8] Kournikova returned for the Du Maurier Open and made it to the third round, before losing to Conchita Martínez. At the 1998 US Open Kournikova reached the fourth round before losing to Arantxa Sánchez Vicario. Her strong year qualified her for the year-end 1998 WTA Tour Championships, but she lost to Monica Seles in the first round. However, with Seles, she won her first WTA doubles title, in Tokyo, beating Mary Joe Fernández and Arantxa Sánchez Vicario in the final. At the end of the season, she was ranked No. 10 in doubles.
At the start of the 1999 season, Kournikova advanced to the fourth round in singles before losing to Mary Pierce. However, Kournikova won her first doubles Grand Slam title, partnering Martina Hingis. The two defeated Lindsay Davenport and Natasha Zvereva in the final. At the Tier I Family Circle Cup, Kournikova reached her second WTA Tour final, but lost to Martina Hingis.[10] She then defeated Jennifer Capriati, Lindsay Davenport and Patty Schnyder on her route to the Bausch & Lomb Championships semifinals, losing to Ruxandra Dragomir. At The French Open, Kournikova reached the fourth round before losing to eventual champion Steffi Graf.[10] Once the grass-court season commenced in England, Kournikova lost to Nathalie Tauziat in the semifinals in Eastbourne. At Wimbledon, Kournikova lost to Venus Williams in the fourth round. She also reached the final in mixed doubles, partnering with Jonas Björkman, but they lost to Leander Paes and Lisa Raymond. Kournikova again qualified for year-end WTA Tour Championships, but lost to Mary Pierce in the first round, and ended the season as World No. 12.
While Kournikova had a successful singles season, she was even more successful in doubles. After their victory at the Australian Open, she and Martina Hingis won tournaments in Indian Wells, Rome, Eastbourne and the WTA Tour Championshiops, and reached the final of The French Open where they lost to Serena and Venus Williams. Partnering with Elena Likhovtseva, Kournikova also reached the final in Stanford. On 22 November 1999 she reached the World No. 1 ranking in doubles, and ended the season at this ranking. Anna Kournikova and Martina Hingis were presented with the WTA Award for Doubles Team of the Year.
Kournikova opened her 2000 season winning the Gold Coast Open doubles tournament partnering with Julie Halard. She then reached the singles semifinals at the Medibank International Sydney, losing to Lindsay Davenport. At the 2000 Australian Open, she reached the fourth round in singles and the semifinals in doubles. That season, Kournikova reached eight semifinals (Sydney, Scottsdale, Stanford, San Diego, Luxembourg, Leipzig and 2000 WTA Tour Championships), seven quarterfinals (Gold Coast, Tokyo, Amelia Island, Hamburg, Eastbourne, Zürich and Philadelphia) and one final. On 20 November 2000 she broke into top 10 for the first time, reaching No. 8. She was also ranked #4 in doubles at the end of the season. Kournikova was once again, more successful in doubles. She reached the final of the 2000 US Open in mixed doubles, partnering with Max Mirnyi, but they lost to Jared Palmer and Arantxa Sánchez Vicario. She also won six doubles titles — Gold Coast (with Julie Halard), Hamburg (with Natasha Zvereva), Filderstadt, Zürich, Philadelphia and the 2000 WTA Tour Championships (with Martina Hingis).
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