Two-time defending champion Martina Hingis defeated Amélie Mauresmo in the final, 6–2, 6–3 to win the women's singles tennis title at the 1999 Australian Open. With the win, she joined Margaret Court, Evonne Goolagong, Steffi Graf, and Monica Seles as the only women to win three consecutive Australian Open titles. Hingis also became the only woman to win three consecutive Australian Open titles in singles and doubles simultaneously.
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.
Steffi Graf defeated Martina Hingis in the final, 4–6, 7–5, 6–2 to win the women's singles tennis title at the 1999 French Open. It was her Open Era record-extending 22nd and final major singles title, and she equaled Chris Evert's record of nine French Open final appearances. Graf also became the first player in the Open Era to defeat the top-three ranked players at the same major; defeating world No. 2 Lindsay Davenport in the quarterfinals, No. 3 Seles in the semifinals and No. 1 Hingis in the final. Hingis was attempting to complete the career Grand Slam in singles.
Iva Majoli defeated Martina Hingis in the final, 6–4, 6–2 to win the women's singles tennis title at the 1997 French Open. Majoli became the first Croat to win a major title. This was the only major match Hingis lost in the 1997 season, preventing her from achieving the Grand Slam. Hingis was on a 35-match winning streak, dating to the start of the season in Sydney.
Defending champion Steffi Graf defeated Arantxa Sánchez Vicario in a rematch of the previous year's final, 6–3, 6–7(4–7), 10–8 to win the women's singles tennis title at the 1996 French Open. With the win, Graf claimed her 19th major singles title, surpassing Chris Evert and Martina Navratilova's Open Era record.
Martina Hingis defeated Mary Pierce in the final, 6–2, 6–2 to win the women's singles tennis title at the 1997 Australian Open. She did not lose a set during the tournament. Hingis became the youngest woman to win a major singles title since Lottie Dod at the 1887 Wimbledon Championships.
Defending champion Martina Hingis defeated Conchita Martínez in the final, 6–3, 6–3 to win the women's singles tennis title at the 1998 Australian Open.
Martina Hingis defeated Venus Williams in the final, 6–0, 6–4 to win the women's singles tennis title at the 1997 US Open. She did not drop a set during the tournament. By reaching the final, Hingis became the seventh woman, to reach all four major singles finals in a calendar year. She also became the youngest woman to reach each major final, and the youngest woman to win three majors in a calendar year. Williams was the first unseeded player in the Open Era to reach the final.
Lindsay Davenport defeated the defending champion Martina Hingis in the final, 6–3, 7–5 to win the women's singles tennis title at the 1998 US Open. The final was a rematch of the previous year's semifinal. Davenport did not drop a set during the tournament.
Martina Hingis defeated Jana Novotná in the final, 2–6, 6–3, 6–3 to win the ladies' singles tennis title at the 1997 Wimbledon Championships. At 16 years and 278 days old, Hingis became the youngest person to win a Wimbledon singles title since Lottie Dod in 1887.
Martina Hingis defeated Monica Seles in the final, 6–2, 6–1 to win the women's singles tennis title at the 1997 Miami Open. At 16 years and 6 months, Hingis became the youngest-ever world No. 1 player in women's singles. This marked the first time that neither Steffi Graf, Seles nor Arantxa Sánchez Vicario were ranked No. 1 since August 17, 1987.
Martina Hingis won the singles tennis title at the 1997 Pan Pacific Open via walkover walkover after Steffi Graf withdrew from the final.
Martina Hingis defeated the defending champion Lindsay Davenport in the final, 6–3, 6–4 to win the women's singles tennis title at the 1998 Indian Wells Masters.
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.
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 Bank of the West Classic singles was the singles event of the twenty-eighth edition of the first 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.
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 defending champion, but had retired after the TIG Classic.
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.
Martina Hingis 
Venus Williams 
