Serena Williams defeated Martina Hingis in the final, 6–3, 7–6(7–4) to win the women's singles tennis title at the 1999 US Open. It was her first major singles title, the first of an eventual Open Era joint-record six US Open titles, and the first of an eventual Open Era record 23 major singles titles. Williams became the first African American woman in the Open Era to win a singles major.
Venus Williams defeated Lindsay Davenport in the final, 6–4, 7–5 to win the women's singles tennis title at the 2000 US Open. It was her second major singles title, and she became the second woman to win Wimbledon, the Olympics, and the US Open in the same season.
Defending champion Martina Hingis won the women's singles tennis title at the 2000 Canadian Open after Serena Williams retired from the final due to a left foot injury, with the score at 0–6, 6–3, 3–0.
The singles competition of the 2001 Britannic Asset Management International Championships was part of the 27th edition of the Eastbourne International tennis tournament, Tier II of the 2001 WTA Tour. Julie Halard-Decugis was the defending champion but did not compete that year. Lindsay Davenport won in the final 6–2, 6–0 against Magüi Serna.
Serena Williams defeated Kim Clijsters in the final, 4–6, 6–4, 6–2 to win the women's singles tennis title at the 2001 Indian Wells Open. This would be the final time Williams would attend the Indian Wells Open until 2015, due to a boycott of the tournament by both Williams sisters in protest of racist remarks by crowd members; Venus Williams would return to the tournament until 2016.
Lindsay Davenport defeated the defending champion Martina Hingis in a rematch of the previous year's final, 6–4, 6–2 to win the singles tennis title at the 1999 WTA Tour Championships.
The 1999 Open Gaz de France singles was the singles event of the seventh edition of the Open GDF Suez; a WTA Tier II tournament held in Paris, France. Mary Pierce was the defending champion but did not compete that year.
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.
Venus Williams defeated Martina Hingis in the final, 6–3, 6–4 to win the singles tennis title at the 1999 European Indoor Championships.
There was no defending champion, due to the cancellation of the semifinals in 1998 due to rain.
Julie Halard-Decugis was the defending champion, but was defeated in the quarterfinals by Tamarine Tanasugarn.
The 1999 WTA Madrid Open singles was the singles event of the fourth edition of the Madrid Open, a WTA Tier III tournament held in Madrid, Spain and part of the European clay court season. Patty Schnyder was the defending champion but she was defeated in the second round by Paola Suárez.
The 1999 Pilot Pen Tennis singles was the singles event of the seventeenth edition of the final tournament in the US Open Series. Steffi Graf was the reigning champion, but had retired after the TIG Classic.
The 1999 Toyota Princess Cup singles was the tennis singles event of the third edition of the first hardcourt tournament after the US Open. Monica Seles was the two-time defending champion, but was defeated by Lindsay Davenport in the final to win the title.
The 1999 Toyota Princess Cup doubles was the tennis doubles event of the third edition of the first hardcourt tournament after the US Open. Anna Kournikova and Monica Seles were the reigning champions, but neither competed this time.
Sandrine Testud was the defending champion, but was defeated by Martina Hingis in the semifinals.
The 1999 Advanta Championships of Philadelphia singles was the tennis singles event of the seventeenth edition of the Advanta Championships of Philadelphia; a WTA Tier II tournament held in Philadelphia. Steffi Graf was the defending champion but retired after Wimbledon earlier in the year.
Julie Halard-Decugis and Ai Sugiyama were the defending champions, but did not compete this year.
Martina Hingis and Anna Kournikova were the defending champions, but none of them competed this year.
Lindsay Davenport was the defending champion, but did not compete this year.
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Serena Williams 
Julie Halard-Decugis 
