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.
Nicole Arendt and Ai Sugiyama were the defending champions but they competed with different partners that year, Arendt with Liezel Huber and Sugiyama with Elena Tatarkova.
Serena Williams and Venus Williams were the defending champions, but Serena withdrew from the tournament and Venus chose not to participate with another player.
Martina Hingis and Anna Kournikova defeated Daniela Hantuchová and Arantxa Sánchez Vicario 6–2, 6–7(4–7), 6–1 in the final to win the title.
The 1998 du Maurier Open women's singles was the women's singles event of the one hundred and ninth edition of the Canadian Open; a WTA Tier I tournament and the most prestigious women's tennis tournament held in Canada. Monica Seles was the defending champion and won in the final 6–3, 6–2 against Arantxa Sánchez Vicario.
Monica Seles and Ai Sugiyama were the defending champions but only Seles competed that year with Anna Kournikova.
The 1999 US Open mixed doubles was the mixed doubles event of the hundred-and-ninth edition of the US Open, the fourth and last Grand Slam of the year. Serena Williams and Max Mirnyi were the defending champions but did not compete that year.
Serena and Venus Williams defeated Martina Hingis and Anna Kournikova in the final, 6–3, 6–7(2–7), 8–6 to win the women's doubles tennis title at the 1999 French Open. It was the first major title for the Williams sisters, and would be their first step towards completing the career Golden Slam in doubles.
The 1999 Italian Open doubles was the doubles event of the fifty-fifth edition of the tennis tournament played at Rome, Italy, the most prestigious tennis tournament in Southern Europe. It was the fifth WTA Tier I tournament of the year, and part of the European claycourt season. Virginia Ruano Pascual and Paola Suárez were the defending champions, but lost to Martina Hingis and Anna Kournikova in the quarterfinals.
Rennae Stubbs and Jared Palmer were the defending champions but only Stubbs competed that year with Todd Woodbridge.
Rennae Stubbs and Jared Palmer defeated 1993 champions Arantxa Sánchez Vicario and Todd Woodbridge in the final, 7–5, 7–6(7–3), to win the mixed doubles tennis title at the 2000 Australian Open. By winning the title, Stubbs won her second Grand Slam title, after she won her first in Women's Doubles earlier in the week, and Palmer won his first major Mixed Doubles title. Mariaan de Swardt and David Adams were the defending champions, but De Swardt chose not to defend her title and Adams played with Kristie Boogert. Adams and Boogert lost to Sánchez Vicario and Woodbridge in the semifinals.
Mahesh Bhupathi and Max Mirnyi were the defending champions, but lost in the quarterfinals to Michaël Llodra and Fabrice Santoro.
Wayne Black and Kevin Ullyett were the defending champions, but lost in the quarterfinals to Mahesh Bhupati and Max Mirnyi.
Defending champion Martina Hingis and her partner Mirjana Lučić defeated the other defending champion Natasha Zvereva and her partner Lindsay Davenport in the final, 6–4, 2–6, 6–3 to win the women's doubles tennis title at the 1998 Australian Open. It was the first step in an eventual Grand Slam for Hingis.
Martina Hingis and Jana Novotná defeated the defending champion Natasha Zvereva and her partner Lindsay Davenport in the final, 6–1, 7–6(7–4) to win the women's doubles tennis title at the 1998 French Open. It was the second step in an eventual Grand Slam for Hingis.
Donald Johnson and Kimberly Po-Messerli were the defending champions but lost in the quarterfinals to Leoš Friedl and Daniela Hantuchová.
Serena Williams and Venus Williams were the defending champions, but did not compete this year.
The 2000 du Maurier Open women's doubles was the women's doubles event of the one hundred and eleventh edition of the Canadian Open; a WTA Tier I tournament and the most prestigious women's tennis tournament held in Canada. Jana Novotná and Mary Pierce were the defending champions, but Novotná retired from professional tennis in 1999 and Pierce did not compete at the tournament. Martina Hingis and Nathalie Tauziat won the title by defeating Julie Halard-Decugis and Ai Sugiyama 6–3, 3–6, 6–4 in the final. It was the 11th title for Hingis and the 21st title for Tauziat in their respective doubles careers.
Virginia Ruano Pascual and Tomás Carbonell were the defending champions, but had different outcomes. Ruano Pascual teamed up with Gastón Etlis and lost in second round to Cara and Wayne Black, while Carbonell did not compete this year due to retiring from professional tennis in 2001.
Arantxa Sánchez Vicario and Jared Palmer were the defending champions, but lost in the quarterfinals to Ai Sugiyama and Ellis Ferreira.
Alexandra Fusai and Nathalie Tauziat were the defending champions, but lost in quarterfinals to Nicole Arendt and Manon Bollegraf.
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Arantxa Sánchez Vicario 
Jared Palmer 
Anna Kournikova 
Max Mirnyi 
