Jana Novotná was the defending champion but lost in the quarterfinals to Lindsay Davenport.
Lisa Raymond and Rennae Stubbs were the defending champions and won in the final 6–3, 7–5 against Lindsay Davenport and Jana Novotná.
Martina Hingis was the defending champion but lost in the quarterfinals to Steffi Graf.
The 1999 Sydney International women's singles was the singles event of the fourteenth edition of the ASB Classic; a WTA Tier II tournament and the second most prestigious women's tennis tournament held in Australia. Arantxa Sánchez Vicario was the defending champion but lost in the quarterfinals to Barbara Schett.
Martina Hingis defeated Amanda Coetzer in the final, 6–2, 6–1 to win the singles tennis title at the 1999 Pan Pacific Open.
The 1999 Toray Pan Pacific Open doubles was the doubles event of the twenty-fourth edition of the Toray Pan Pacific Open Tennis Tournament, the first WTA Tier I tournament of the year. Martina Hingis and Mirjana Lučić were the defending champions but only Hingis competed that year with Jana Novotná.
Serena Williams defeated Steffi Graf in the final, 6–3, 3–6, 7–5 to win the women's singles tennis title at the 1999 Indian Wells Open. It was the second and last time that the two would contest a professional match.
The 1999 Evert Cup doubles was the doubles event of the eleventh edition of the tennis tournament played at Indian Wells, California, United States. It was the second WTA Tier I tournament of the year, and part of the US Spring tennis season. Lindsay Davenport and Natasha Zvereva were the defending champions but lost in the quarterfinals to Serena Williams and Venus Williams.
Defending champion Venus Williams defeated her sister Serena in the final, 6–1, 4–6, 6–4 to win the women's singles tennis title at the 1999 Miami Open.
The 1999 Betty Barclay Cup singles was the singles event of the fifteenth edition of the Betty Barclay Cup, a WTA Tier II tournament held in Hamburg, Germany and part of the European claycourt season. Martina Hingis was the defending champion but she did not compete that year.
Venus Williams defeated Mary Pierce in the final, 6–4, 6–2 to win the women's singles tennis title at the 1999 Italian Open.
Venus Williams defeated Martina Hingis in the final, 6–3, 6–4 to win the singles tennis title at the 1999 European Indoor Championships.
The 1999 TIG Classic singles was the singles event of the twentieth edition of the second tournament in the US Open Series.
The 1999 Acura Classic singles was the singles event of the twentieth edition of the third tournament in the US Open Series.
Sandrine Testud was the defending champion, but was defeated by Martina Hingis in the semifinals.
The 1999 Porsche Tennis Grand Prix doubles was the tennis doubles event at the 1999 Porsche Tennis Grand Prix, the twenty-second edition of the most prestigious tournament in Baden-Württemberg. Lindsay Davenport and Natasha Zvereva were the defending champions, but they did not compete together this year. Davenport competed with Martina Hingis as the first seed, while Zvereva competed with Elena Tatarkova. Davenport and Hingis withdrew in the quarterfinals due to Davenport having a wrist injury, whilst Tatarkova and Zvereva were knocked out in the first round.
Martina Hingis was the defending champion, but did not compete this year. Hingis would retire from professional tennis one month later.
Martina Hingis defeated Lindsay Davenport in the final, 6–4, 4–6, 7–5 to win the singles tennis title at the 2000 Swisscom Challenge.
Lindsay Davenport was the defending champion, and successfully defended her title, by defeating Martina Hingis 7–6(9–7), 6–4 in the final.
Martina Hingis was the two-time defending champion, but retired in the semifinals against Lindsay Davenport.
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Lindsay Davenport 
Martina Hingis 
