| Singles | |
|---|---|
| 1999 Toyota Princess Cup | |
| Champion |  Lindsay Davenport |
| Runner-up | Monica Seles |
| Final score | 7–5, 7–6(7–1) |
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.
Lindsay Davenport (champion) Monica Seles (final)
Julie Halard-Decugis (quarterfinals)
Amanda Coetzer (quarterfinals) Amélie Mauresmo (quarterfinals)
Conchita Martínez (quarterfinals) Amy Frazier (semifinals)
Ai Sugiyama (semifinals)| Semifinals | Final | ||||||||||||
| 1 | Lindsay Davenport | 6 | 6 | ||||||||||
| 7 | Amy Frazier | 2 | 1 | ||||||||||
| 1 | Lindsay Davenport | 7 | 77 | ||||||||||
| 2 | Monica Seles | 5 | 61 | ||||||||||
| 8 | Ai Sugiyama | 3 | 63 | ||||||||||
| 2 | Monica Seles | 6 | 77 | ||||||||||
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 1 | L Davenport | 6 | 6 | ||||||||||||||||||||||||
| C Morariu | 6 | 5 | 1 |  A Smashnova | 0 | 1 | |||||||||||||||||||||
| A Smashnova | 2 | 7 | 6 | 1 | L Davenport | 6 | 6 | ||||||||||||||||||||
| Q | S Asagoe | 6 | 6 | 5 | A Mauresmo | 1 | 1 | ||||||||||||||||||||
| Q |  V Webb | 4 | 1 | Q | S Asagoe | 2 | 5 | ||||||||||||||||||||
| LL | T Singian | 6 | 3 | 1 | 5 | A Mauresmo | 6 | 7 | |||||||||||||||||||
| 5 | A Mauresmo | 2 | 6 | 6 | 1 | L Davenport | 6 | 6 | |||||||||||||||||||
| 7 | A Frazier | 2 | 1 | ||||||||||||||||||||||||
| 4 | A Coetzer | 4 | 6 | 6 | |||||||||||||||||||||||
 O Barabanschikova | 4 | 2 | M Drake | 6 | 3 | 4 | |||||||||||||||||||||
| M Drake | 6 | 6 | 4 | A Coetzer | 0 | 4 | |||||||||||||||||||||
 S Talaja | 64 | 6 | 3 | 7 | A Frazier | 6 | 6 | ||||||||||||||||||||
| Q | Y Yoshida | 77 | 4 | 6 | Q | Y Yoshida | 3 | 2 | |||||||||||||||||||
| LL |  S-h Park | 1 | 4 | 7 | A Frazier | 6 | 6 | ||||||||||||||||||||
| 7 | A Frazier | 6 | 6 | ||||||||||||||||||||||||
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 8 | A Sugiyama | 6 | 6 | ||||||||||||||||||||||||
 T Tanasugarn | 3 | 3 | 8 | A Sugiyama | 6 | 6 | |||||||||||||||||||||
| WC | M Viele | 3 | 1 | J Chi | 2 | 4 | |||||||||||||||||||||
| J Chi | 6 | 6 | 8 | A Sugiyama | 6 | 7 | |||||||||||||||||||||
 N Pratt | 6 | 7 | 3 | J Halard-Decugis | 2 | 5 | |||||||||||||||||||||
| M Tu | 3 | 5 | N Pratt | 1 | 0 | ||||||||||||||||||||||
| 3 | J Halard-Decugis | 6 | 6 | ||||||||||||||||||||||||
| 8 | A Sugiyama | 3 | 63 | ||||||||||||||||||||||||
| 6 | C Martínez | 6 | 6 | 2 | M Seles | 6 | 77 | ||||||||||||||||||||
| J Dokic | 3 | 2 | 6 | C Martínez | 6 | 6 | |||||||||||||||||||||
| WC | M Saeki | 1 | 1 |  T Panova | 1 | 1 | |||||||||||||||||||||
| T Panova | 6 | 6 | 6 | C Martínez | 2 | 0 | |||||||||||||||||||||
| T Snyder | 1 | 1 | 2 | M Seles | 6 | 6 | |||||||||||||||||||||
| Q |  M Vavrinec | 6 | 6 | Q | M Vavrinec | 2 | 0 | ||||||||||||||||||||
| 2 | M Seles | 6 | 6 | ||||||||||||||||||||||||
Miroslava Vavrinec (Qualifier) Kerry-Anne Guse (first round) Shinobu Asagoe (Qualifier) Yuka Yoshida (Qualifier) Renata Kolbovic (second round) Vanessa Webb (Qualifier)
Petra Rampre (second round) Tracy Singian (qualifying competition)| First round | Second round | Qualifying competition | ||||||||||||||||||
| 1 | Miroslava Vavrinec | 6 | 6 | |||||||||||||||||
| Alt |  Catherine Turinsky | 3 | 2 | |||||||||||||||||
| 1 | Miroslava Vavrinec | 6 | 6 | |||||||||||||||||
| Madoka Kuki | 3 | 3 | ||||||||||||||||||
| Madoka Kuki | 6 | 6 | ||||||||||||||||||
| WC | Azusa Konishi | 1 | 2 | |||||||||||||||||
| 1 | Miroslava Vavrinec | 6 | 7 | |||||||||||||||||
| Park Sung-hee | 1 | 5 | ||||||||||||||||||
| Park Sung-hee | 6 | 6 | ||||||||||||||||||
| Maiko Inoue | 3 | 0 | ||||||||||||||||||
| Park Sung-hee | 3 | 6 | 6 | |||||||||||||||||
| 7 | Petra Rampre | 6 | 1 | 1 | ||||||||||||||||
| Tomoe Hotta | 2 | 1 | ||||||||||||||||||
| 7 | Petra Rampre | 6 | 6 | |||||||||||||||||
| First round | Second round | Qualifying competition | ||||||||||||||||||
| 3 | Shinobu Asagoe | 6 | 6 | |||||||||||||||||
 Iroda Tulyaganova | 0 | 2 | ||||||||||||||||||
| 3 | Shinobu Asagoe | 7 | 6 | |||||||||||||||||
| Vanessa Henke | 5 | 3 | ||||||||||||||||||
| Catherine Barclay | 4 | 1 | ||||||||||||||||||
| Vanessa Henke | 6 | 6 | ||||||||||||||||||
| 3 | Shinobu Asagoe | 2 | 77 | 7 | ||||||||||||||||
| Haruka Inoue | 6 | 62 | 5 | |||||||||||||||||
| Kim Eun-ha | 62 | 1 | ||||||||||||||||||
| Haruka Inoue | 77 | 6 | ||||||||||||||||||
| Haruka Inoue | 2 | 6 | 6 | |||||||||||||||||
| 5 | Renata Kolbovic | 6 | 3 | 2 | ||||||||||||||||
| WC | Remi Uda | 2 | 3 | |||||||||||||||||
| 5 | Renata Kolbovic | 6 | 6 | |||||||||||||||||
| First round | Second round | Qualifying competition | ||||||||||||||||||
| 8 | Tracy Singian | 6 | 7 | |||||||||||||||||
| Hiroko Mochizuki | 3 | 5 | ||||||||||||||||||
| 8 | Tracy Singian | 6 | 6 | |||||||||||||||||
| WC | Rika Fujiwara | 3 | 3 | |||||||||||||||||
| WC | Rika Fujiwara | 67 | 6 | 6 | ||||||||||||||||
| WC | Kaori Aoyama | 79 | 3 | 2 | ||||||||||||||||
| 8 | Tracy Singian | 4 | 3 | |||||||||||||||||
| 4 | Yuka Yoshida | 6 | 6 | |||||||||||||||||
| Akiko Morigami | 5 | 4 | ||||||||||||||||||
| Cho Yoon-jeong | 7 | 6 | ||||||||||||||||||
| Cho Yoon-jeong | 1 | 1 | ||||||||||||||||||
| 4 | Yuka Yoshida | 6 | 6 | |||||||||||||||||
| Miyako Ataka | 0 | 1 | ||||||||||||||||||
| 4 | Yuka Yoshida | 6 | 6 | |||||||||||||||||
| First round | Second round | Qualifying competition | ||||||||||||||||||
| 6 | Vanessa Webb | 6 | 6 | |||||||||||||||||
| Yoshiko Sasano | 1 | 3 | ||||||||||||||||||
| 6 | Vanessa Webb | 1 | 6 | 6 | ||||||||||||||||
| Marketa Kochta | 6 | 1 | 3 | |||||||||||||||||
| Marketa Kochta | 6 | 6 | ||||||||||||||||||
| Keiko Nagatomi | 0 | 3 | ||||||||||||||||||
| 6 | Vanessa Webb | 6 | 6 | |||||||||||||||||
| Shiho Hisamatsu | 2 | 1 | ||||||||||||||||||
| Riei Otakeyama | 77 | 6 | ||||||||||||||||||
| Rika Hiraki | 63 | 4 | ||||||||||||||||||
| Riei Otakeyama | 6 | 3 | 3 | |||||||||||||||||
| Shiho Hisamatsu | 4 | 6 | 6 | |||||||||||||||||
| Shiho Hisamatsu | 67 | 6 | 6 | |||||||||||||||||
| 2 | Kerry-Anne Guse | 79 | 3 | 4 | ||||||||||||||||
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.
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.
Venus Williams defeated the defending champion Lindsay Davenport in the final, 6–3, 7–6(7–3) to win the ladies' singles tennis title at the 2000 Wimbledon Championships. It was her first major singles title. Williams lost only one set during the entire tournament, to Martina Hingis in the quarterfinals.
Jennifer Capriati defeated Martina Hingis in the final, 6–4, 6–3 to win the women's singles tennis title at the 2001 Australian Open. With the win, Capriati returned to the top 10 in rankings for the first time since 1993.
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. 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. She did not drop a set during the tournament. Williams was the first unseeded player in the Open Era to reach the final.
Justine Henin won in the final 6–2, 6–2 against Sandrine Testud.
Gabriela Sabatini was the defending champion but did not compete that year.
Jana Novotná was the defending champion but lost in the quarterfinals to Lindsay Davenport.
Monica Seles was the defending champion but lost in the semifinals to Lindsay Davenport.
The 1999 Toray Pan Pacific Open singles was the singles event of the twenty-fourth edition of the Toray Pan Pacific Open Tennis Tournament, the first WTA Tier I tournament of the year. Lindsay Davenport was the defending champion but lost in the quarterfinals to Amanda Coetzer.
The 1999 Lipton Championships women's singles was the women's singles event of the fifteenth edition of the tennis tournament played at Miami, United States. It is the third WTA Tier I tournament of the year, and part of the US Spring tennis season. Venus Williams was the defending champion, and she successfully defending her title by defeating her sister Serena in the final 6–1, 4–6, 6–4.
The 1999 Bausch & Lomb Championships singles was the singles event of the twentieth edition of the Bausch & Lomb Championships; a WTA Tier II tournament held in Amelia Island, Florida, United States, played on green clay. Mary Pierce was the defending champion but lost in the quarterfinals to Conchita Martínez.
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 Torneo Internazionali Femminili di Palermo singles was the singles event of the twelfth edition of the second most prestigious women's tennis tournament held in Italy. Patty Schnyder was the defending champion, but she did not compete this year.
The 1999 Toyota Princess Cup was a women's tennis tournament played on outdoor hard courts in Tokyo, Japan. It was part of Tier II of the 1999 WTA Tour. It was the third edition of the tournament and was held from 20 September through 27 September 1999. First-seeded Lindsay Davenport won the singles title and earned $80,000 first-prize money.
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 defending champions, but neither competed this time.
The 1999 Wismilak International singles was the singles event of the fifth edition of the most prestigious women's tennis tournament held in Southeast Asia. It was not played the previous year, so there was no defending champion.
The 1999 Wismilak International doubles was the doubles event of the fifth edition of the most prestigious women's tennis tournament held in Southeast Asia. It was not played the previous year, so there was no defending champion.
Lindsay Davenport was the defending champion and successfully defended her title by defeating Silvia Farina Elia 7–5, 7–5 in the final.
Teryn Ashley and Abigail Spears were the defending champions, but Spears decided to compete in Gold Coast at the same week. Ashley teamed up with Shenay Perry and lost in first round to Iveta Benešová and Renata Voráčová.