Match log updated: 2026-08-30 18:41 UTC
Anna Kournikova — WTA Match Log
Main draw matches: 305 | W: 184 | L: 121 | Win %: 60.3%
| Opponent | Score | Result | H2H | Match Data | Date ↓ | Round | Tournament | Category | Surface |
|---|---|---|---|---|---|---|---|---|---|
| Conchita Martínez | 4-6 1-1 (ret.) | L | H2H | Match data | Apr 9, 2003* | R64 | Charleston Open | Tier I → modern equivalent WTA 1000 | Clay |
| Iva Majoli | 4-6 6-4 4-6 | L | H2H | Match data | Apr 3, 2003* | R32 | Sarasota | Tier IV → modern equivalent WTA 250 | Clay |
| Dinara Safina | 1-6 4-6 | L | H2H | Match data | Mar 20, 2003* | R128 | Miami Open | Tier I → modern equivalent WTA 1000 | Hard |
| Justine Henin | 0-6 1-6 | L | H2H | Match data | Jan 17, 2003* | R64 | Australian Open | Grand Slam | Hard |
| Henrieta Nagyova | 6-1 6-2 | W | H2H | Match data | Jan 15, 2003* | R128 | Australian Open | Grand Slam | Hard |
| Janette Husarova | 4-6 6-2 1-6 | L | H2H | Match data | Jan 9, 2003* | R32 | Sydney International | Tier II → modern equivalent WTA 500 | Hard |
| Nadia Petrova | (w/o) | L | H2H | Match data | Oct 4, 2002* | R16 | Moscow | Tier I → modern equivalent WTA 1000 | Carpet |
| Marie-Gayanay Mikaelian | 6-4 6-3 | W | H2H | Match data | Oct 3, 2002* | R32 | Moscow | Tier I → modern equivalent WTA 1000 | Carpet |
| Anna Smashnova | 2-6 3-6 | L | H2H | Match data | Sep 15, 2002* | F | Shanghai | Tier IV → modern equivalent WTA 250 | Hard |
| Ai Sugiyama | 6-4 7-5 | W | H2H | Match data | Sep 14, 2002* | SF | Shanghai | Tier IV → modern equivalent WTA 250 | Hard |
| Jelena Kostanic Tosic | 7-5 6-4 | W | H2H | Match data | Sep 14, 2002* | QF | Shanghai | Tier IV → modern equivalent WTA 250 | Hard |
| Jie Zheng | 6-4 7-6(4) | W | H2H | Match data | Sep 13, 2002* | R16 | Shanghai | Tier IV → modern equivalent WTA 250 | Hard |
| Mireille Dittmann | 6-1 6-4 | W | H2H | Match data | Sep 12, 2002* | R32 | Shanghai | Tier IV → modern equivalent WTA 250 | Hard |
| Angelique Widjaja | 3-6 0-6 | L | H2H | Match data | Aug 28, 2002* | R128 | US Open | Grand Slam | Hard |
| Virginia Ruano Pascual | 5-7 1-6 | L | H2H | Match data | Aug 15, 2002* | R32 | Canadian Open | Tier I → modern equivalent WTA 1000 | Hard |
| Saori Obata | 6-3 6-1 | W | H2H | Match data | Aug 14, 2002* | R64 | Canadian Open | Tier I → modern equivalent WTA 1000 | Hard |
| Jelena Dokic | 7-6(6) 6-7(2) 0-6 | L | H2H | Match data | Aug 3, 2002* | SF | San Diego | Tier II → modern equivalent WTA 500 | Hard |
| Anna Smashnova | 1-6 6-3 6-4 | W | H2H | Match data | Aug 3, 2002* | QF | San Diego | Tier II → modern equivalent WTA 500 | Hard |
| Conchita Martínez | 1-6 6-2 6-1 | W | H2H | Match data | Aug 2, 2002* | R16 | San Diego | Tier II → modern equivalent WTA 500 | Hard |
| Jennifer Hopkins | 6-2 6-4 | W | H2H | Match data | Aug 1, 2002* | R32 | San Diego | Tier II → modern equivalent WTA 500 | Hard |
| Alexandra Stevenson | 6-0 6-1 | W | H2H | Match data | Jul 31, 2002* | R64 | San Diego | Tier II → modern equivalent WTA 500 | Hard |
| Venus Williams | 3-6 4-6 | L | H2H | Match data | Jul 27, 2002* | QF | Stanford | Tier II → modern equivalent WTA 500 | Hard |
| Wynne Prakusya | 7-5 6-4 | W | H2H | Match data | Jul 26, 2002* | R16 | Stanford | Tier II → modern equivalent WTA 500 | Hard |
| Anna Smashnova | 6-3 6-2 | W | H2H | Match data | Jul 25, 2002* | R32 | Stanford | Tier II → modern equivalent WTA 500 | Hard |
| Tatiana Panova | 1-6 6-4 4-6 | L | H2H | Match data | Jun 26, 2002* | R128 | Wimbledon | Grand Slam | Grass |
| Rita Grande | 7-6(4) 3-6 1-6 | L | H2H | Match data | Jun 20, 2002* | R32 | Eastbourne Open | Tier II → modern equivalent WTA 500 | Grass |
| Christina Wheeler | 4-6 3-6 | L | H2H | Match data | May 29, 2002* | R128 | Roland Garros | Grand Slam | Clay |
| Petra Mandula | 6-7(5) 2-6 | L | H2H | Match data | May 23, 2002* | R32 | Strasbourg Open | Tier III → modern equivalent WTA 250 | Clay |
| Virginia Ruano Pascual | 3-6 2-6 | L | H2H | Match data | May 17, 2002* | R16 | Italian Open | Tier I → modern equivalent WTA 1000 | Clay |
| Lilia Osterloh | 6-1 4-6 6-1 | W | H2H | Match data | May 16, 2002* | R32 | Italian Open | Tier I → modern equivalent WTA 1000 | Clay |
| Marta Marrero | 6-3 6-3 | W | H2H | Match data | May 15, 2002* | R64 | Italian Open | Tier I → modern equivalent WTA 1000 | Clay |
| Svetlana Kuznetsova | 6-4 4-6 2-5 (ret.) | L | H2H | Match data | May 9, 2002* | R32 | Warsaw | Tier III → modern equivalent WTA 250 | Clay |
| Tina Pisnik | 7-6(1) 3-6 3-6 | L | H2H | Match data | May 3, 2002* | R16 | Bol | Tier III → modern equivalent WTA 250 | Clay |
| Julia Vakulenko | 6-7(3) 6-2 6-2 | W | H2H | Match data | May 2, 2002* | R32 | Bol | Tier III → modern equivalent WTA 250 | Clay |
| Conchita Martínez | 6-7(5) 1-6 | L | H2H | Match data | Apr 17, 2002* | R64 | Charleston Open | Tier I → modern equivalent WTA 1000 | Clay |
| Paola Suarez | 4-6 1-6 | L | H2H | Match data | Apr 10, 2002* | R64 | Amelia Island | Tier II → modern equivalent WTA 500 | Clay |
| Eleni Daniilidou | 5-7 3-6 | L | H2H | Match data | Mar 19, 2002* | R128 | Miami Open | Tier I → modern equivalent WTA 1000 | Hard |
| Lilia Osterloh | 1-6 4-6 | L | H2H | Match data | Mar 6, 2002 | R128 | Indian Wells Open | Tier I → modern equivalent WTA 1000 | Hard |
| Katarina Srebotnik | 7-5 3-6 1-6 | L | H2H | Match data | Mar 2, 2002* | SF | Acapulco | Tier III → modern equivalent WTA 250 | Clay |
| Janette Husarova | 6-3 6-4 | W | H2H | Match data | Mar 2, 2002* | QF | Acapulco | Tier III → modern equivalent WTA 250 | Clay |
| Tathiana Garbin | 6-1 6-2 | W | H2H | Match data | Mar 1, 2002* | R16 | Acapulco | Tier III → modern equivalent WTA 250 | Clay |
| Mariana Diaz-Oliva | 6-4 7-5 | W | H2H | Match data | Feb 28, 2002* | R32 | Acapulco | Tier III → modern equivalent WTA 250 | Clay |
| Venus Williams | 2-6 6-7(3) | L | H2H | Match data | Feb 22, 2002* | R16 | Dubai Tennis Championships | Tier II → modern equivalent WTA 500 | Hard |
| Selima Sfar | 6-7(3) 6-2 6-4 | W | H2H | Match data | Feb 21, 2002* | R32 | Dubai Tennis Championships | Tier II → modern equivalent WTA 500 | Hard |
| Venus Williams | 5-7 0-6 | L | H2H | Match data | Feb 15, 2002* | R16 | Antwerp | Tier II → modern equivalent WTA 500 | Carpet |
| Marlene Weingartner | 6-2 6-1 | W | H2H | Match data | Feb 14, 2002* | R32 | Antwerp | Tier II → modern equivalent WTA 500 | Carpet |
| Amélie Mauresmo | 3-6 5-7 | L | H2H | Match data | Feb 9, 2002* | R16 | Paris | Tier II → modern equivalent WTA 500 | Carpet |
| Emmanuelle Gagliardi | 6-7(3) 6-4 6-4 | W | H2H | Match data | Feb 8, 2002* | R32 | Paris | Tier II → modern equivalent WTA 500 | Carpet |
| Monica Seles | 3-6 6-3 3-6 | L | H2H | Match data | Feb 3, 2002* | SF | Pan Pacific Open | Tier I → modern equivalent WTA 1000 | Carpet |
| Anne Kremer | 6-4 6-2 | W | H2H | Match data | Feb 2, 2002* | QF | Pan Pacific Open | Tier I → modern equivalent WTA 1000 | Carpet |
| Elena Dementieva | 7-6(4) 7-6(5) | W | H2H | Match data | Feb 1, 2002* | R16 | Pan Pacific Open | Tier I → modern equivalent WTA 1000 | Carpet |
| Cristina Torrens Valero | 6-3 6-0 | W | H2H | Match data | Jan 31, 2002* | R32 | Pan Pacific Open | Tier I → modern equivalent WTA 1000 | Carpet |
| Justine Henin | 2-6 5-7 | L | H2H | Match data | Jan 16, 2002* | R128 | Australian Open | Grand Slam | Hard |
| Serena Williams | 2-6 6-4 3-6 | L | H2H | Match data | Jan 10, 2002* | R16 | Sydney International | Tier II → modern equivalent WTA 500 | Hard |
| Angeles Montolio | 6-4 6-2 | W | H2H | Match data | Jan 9, 2002* | R32 | Sydney International | Tier II → modern equivalent WTA 500 | Hard |
| Anna Smashnova | 1-6 4-6 | L | H2H | Match data | Jan 5, 2002* | SF | ASB Classic | Tier IV → modern equivalent WTA 250 | Hard |
| Emmanuelle Gagliardi | 2-6 6-4 7-5 | W | H2H | Match data | Jan 5, 2002* | QF | ASB Classic | Tier IV → modern equivalent WTA 250 | Hard |
| Amy Frazier | 6-4 6-1 | W | H2H | Match data | Jan 4, 2002* | R16 | ASB Classic | Tier IV → modern equivalent WTA 250 | Hard |
| Cara Black | 7-6(6) 6-2 | W | H2H | Match data | Jan 3, 2002* | R32 | ASB Classic | Tier IV → modern equivalent WTA 250 | Hard |
| Kim Clijsters | 5-7 6-7(2) | L | H2H | Match data | Oct 27, 2001* | QF | Luxembourg | Tier III → modern equivalent WTA 250 | Hard |
| Daniela Hantuchova | 6-1 7-6(4) | W | H2H | Match data | Oct 26, 2001* | R16 | Luxembourg | Tier III → modern equivalent WTA 250 | Hard |
| Jana Kandarr | 6-4 7-5 | W | H2H | Match data | Oct 25, 2001* | R32 | Luxembourg | Tier III → modern equivalent WTA 250 | Hard |
| Amanda Coetzer | 0-6 6-4 3-6 | L | H2H | Match data | Oct 18, 2001* | R32 | Zurich | Tier I → modern equivalent WTA 1000 | Hard |
| Anne Kremer | 6-4 2-6 5-7 | L | H2H | Match data | Oct 11, 2001* | R32 | Porsche Tennis Grand Prix | Tier II → modern equivalent WTA 500 | Hard |
| Galina Fokina | 2-6 6-1 2-6 | L | H2H | Match data | Oct 4, 2001* | R32 | Moscow | Tier I → modern equivalent WTA 1000 | Carpet |
| Anastasia Myskina | 4-6 6-3 3-6 | L | H2H | Match data | Sep 28, 2001* | R16 | Leipzig | Tier II → modern equivalent WTA 500 | Carpet |
| Nicole Pratt | 7-6(1) 1-6 3-6 | L | H2H | Match data | Aug 2, 2001* | R32 | San Diego | Tier II → modern equivalent WTA 500 | Hard |
| Amélie Mauresmo | 6-2 6-7(4) 1-6 | L | H2H | Match data | Feb 11, 2001* | QF | Paris | Tier II → modern equivalent WTA 500 | Carpet |
| Sandra Kleinova | 6-0 6-3 | W | H2H | Match data | Feb 10, 2001* | R16 | Paris | Tier II → modern equivalent WTA 500 | Carpet |
| Lindsay Davenport | 1-6 7-6(5) 0-6 | L | H2H | Match data | Feb 3, 2001* | SF | Pan Pacific Open | Tier I → modern equivalent WTA 1000 | Carpet |
| Anne-Gaelle Sidot | 7-6(4) 6-2 | W | H2H | Match data | Feb 3, 2001* | QF | Pan Pacific Open | Tier I → modern equivalent WTA 1000 | Carpet |
| Saori Obata | 7-6(8) 1-6 6-4 | W | H2H | Match data | Feb 2, 2001* | R16 | Pan Pacific Open | Tier I → modern equivalent WTA 1000 | Carpet |
| Lindsay Davenport | 4-6 2-6 | L | H2H | Match data | Jan 26, 2001* | QF | Australian Open | Grand Slam | Hard |
| Barbara Rittner | 6-3 6-1 | W | H2H | Match data | Jan 24, 2001* | R16 | Australian Open | Grand Slam | Hard |
| Barbara Schett | 2-6 6-4 6-3 | W | H2H | Match data | Jan 21, 2001* | R32 | Australian Open | Grand Slam | Hard |
| Rita Kuti-Kis | 6-3 6-4 | W | H2H | Match data | Jan 19, 2001* | R64 | Australian Open | Grand Slam | Hard |
| Daniela Hantuchova | 6-2 7-5 | W | H2H | Match data | Jan 17, 2001* | R128 | Australian Open | Grand Slam | Hard |
| Corina Morariu | 2-6 1-6 | L | H2H | Match data | Jan 11, 2001* | R16 | Sydney International | Tier II → modern equivalent WTA 500 | Hard |
| Elena Bovina | 6-4 6-4 | W | H2H | Match data | Jan 10, 2001* | R32 | Sydney International | Tier II → modern equivalent WTA 500 | Hard |
| Martina Hingis | 6-7(2) 2-6 | L | H2H | Match data | Nov 18, 2000* | SF | WTA Finals | WTA Finals | Carpet |
| Conchita Martínez | 6-4 6-0 | W | H2H | Match data | Nov 18, 2000* | QF | WTA Finals | WTA Finals | Carpet |
| Jennifer Capriati | 6-4 6-4 | W | H2H | Match data | Nov 17, 2000* | R16 | WTA Finals | WTA Finals | Carpet |
| Martina Hingis | 4-6 0-6 | L | H2H | Match data | Nov 9, 2000* | QF | Philadelphia | Tier II → modern equivalent WTA 500 | Carpet |
| Nicole Pratt | 6-0 6-2 | W | H2H | Match data | Nov 8, 2000* | R16 | Philadelphia | Tier II → modern equivalent WTA 500 | Carpet |
| Mashona Washington | 6-2 6-0 | W | H2H | Match data | Nov 7, 2000* | R32 | Philadelphia | Tier II → modern equivalent WTA 500 | Carpet |
| Kim Clijsters | 2-6 3-6 | L | H2H | Match data | Nov 4, 2000* | SF | Leipzig | Tier II → modern equivalent WTA 500 | Carpet |
| Magdalena Maleeva | 6-4 7-5 | W | H2H | Match data | Nov 4, 2000* | QF | Leipzig | Tier II → modern equivalent WTA 500 | Carpet |
| Silvia Farina Elia | 6-3 6-1 | W | H2H | Match data | Nov 3, 2000* | R16 | Leipzig | Tier II → modern equivalent WTA 500 | Carpet |
| Martina Hingis | 3-6 1-6 | L | H2H | Match data | Oct 27, 2000* | F | Moscow | Tier I → modern equivalent WTA 1000 | Carpet |
| Nathalie Tauziat | 6-2 6-1 | W | H2H | Match data | Oct 26, 2000* | SF | Moscow | Tier I → modern equivalent WTA 1000 | Carpet |
| Tatiana Panova | 6-4 6-1 | W | H2H | Match data | Oct 26, 2000* | QF | Moscow | Tier I → modern equivalent WTA 1000 | Carpet |
| Vera Zvonareva | 7-6(4) 6-4 | W | H2H | Match data | Oct 25, 2000* | R16 | Moscow | Tier I → modern equivalent WTA 1000 | Carpet |
| Jennifer Capriati | 6-7(4) 4-6 | L | H2H | Match data | Oct 14, 2000* | QF | Zurich | Tier I → modern equivalent WTA 1000 | Hard |
| Tatiana Panova | 6-3 6-3 | W | H2H | Match data | Oct 13, 2000* | R16 | Zurich | Tier I → modern equivalent WTA 1000 | Hard |
| Kim Clijsters | 4-6 3-6 | L | H2H | Match data | Oct 5, 2000* | R32 | Porsche Tennis Grand Prix | Tier II → modern equivalent WTA 500 | Hard |
| Magdalena Maleeva | 2-6 4-6 | L | H2H | Match data | Sep 28, 2000* | SF | Luxembourg | Tier III → modern equivalent WTA 250 | Carpet |
| Kim Clijsters | 6-7(1) 6-3 6-1 | W | H2H | Match data | Sep 28, 2000* | QF | Luxembourg | Tier III → modern equivalent WTA 250 | Carpet |
| Nadia Petrova | 1-6 7-5 4-1 (ret.) | W | H2H | Match data | Sep 27, 2000* | R16 | Luxembourg | Tier III → modern equivalent WTA 250 | Carpet |
| Justine Henin | 4-6 6-7 | L | H2H | Match data | Aug 22, 2000 | R32 | US Open | Grand Slam | Hard |
| Sandra Kleinova | 6-4 6-1 | W | H2H | Match data | Aug 22, 2000 | R64 | US Open | Grand Slam | Hard |
| Holly Parkinson | 6-2 6-3 | W | H2H | Match data | Aug 22, 2000 | R128 | US Open | Grand Slam | Hard |
| Serena Williams | 3-6 2-6 | L | H2H | Match data | Aug 18, 2000* | R16 | Canadian Open | Tier I → modern equivalent WTA 1000 | Hard |
| Sabine Appelmans | 6-4 6-3 | W | H2H | Match data | Aug 17, 2000* | R32 | Canadian Open | Tier I → modern equivalent WTA 1000 | Hard |
| Cara Black | 6-3 7-6(4) | W | H2H | Match data | Aug 16, 2000* | R64 | Canadian Open | Tier I → modern equivalent WTA 1000 | Hard |
| Monica Seles | 3-6 6-7(2) | L | H2H | Match data | Aug 5, 2000* | SF | San Diego | Tier II → modern equivalent WTA 500 | Hard |
| Nathalie Tauziat | 2-6 6-4 7-5 | W | H2H | Match data | Aug 5, 2000* | QF | San Diego | Tier II → modern equivalent WTA 500 | Hard |
| Lindsay Davenport | 2-6 6-4 7-5 | W | H2H | Match data | Aug 4, 2000* | R16 | San Diego | Tier II → modern equivalent WTA 500 | Hard |
| Alexandra Stevenson | 6-2 6-3 | W | H2H | Match data | Aug 3, 2000* | R32 | San Diego | Tier II → modern equivalent WTA 500 | Hard |
| Venus Williams | 4-6 5-7 | L | H2H | Match data | Jul 29, 2000* | SF | Stanford | Tier II → modern equivalent WTA 500 | Hard |
| Sandrine Testud | 6-3 6-2 | W | H2H | Match data | Jul 29, 2000* | QF | Stanford | Tier II → modern equivalent WTA 500 | Hard |
| Jana Nejedly | 6-1 6-0 | W | H2H | Match data | Jul 28, 2000* | R16 | Stanford | Tier II → modern equivalent WTA 500 | Hard |
| Anne Miller | 6-1 6-2 | W | H2H | Match data | Jul 27, 2000* | R32 | Stanford | Tier II → modern equivalent WTA 500 | Hard |
| Anne-Gaelle Sidot | 3-6 4-6 | L | H2H | Match data | Jun 29, 2000* | R64 | Wimbledon | Grand Slam | Grass |
| Sandrine Testud | 7-5 5-7 6-4 | W | H2H | Match data | Jun 28, 2000* | R128 | Wimbledon | Grand Slam | Grass |
| Chanda Rubin | 5-7 6-0 3-6 | L | H2H | Match data | Jun 24, 2000* | QF | Eastbourne Open | Tier II → modern equivalent WTA 500 | Grass |
| Natasha Zvereva | 6-3 6-1 | W | H2H | Match data | Jun 23, 2000* | R16 | Eastbourne Open | Tier II → modern equivalent WTA 500 | Grass |
| Sylvia Plischke | 2-6 6-4 3-6 | L | H2H | Match data | Jun 1, 2000* | R64 | Roland Garros | Grand Slam | Clay |
| Vanessa Webb | 6-4 6-4 | W | H2H | Match data | May 31, 2000* | R128 | Roland Garros | Grand Slam | Clay |
| Gala Leon Garcia | 4-6 6-4 4-6 | L | H2H | Match data | May 9, 2000* | R32 | Berlin Open | Tier I → modern equivalent WTA 1000 | Clay |
| Martina Hingis | 6-3 2-6 4-6 | L | H2H | Match data | May 5, 2000* | QF | Hamburg Open | Tier II → modern equivalent WTA 500 | Clay |
| Sarah Pitkowski-Malcor | 6-3 6-0 | W | H2H | Match data | May 4, 2000* | R16 | Hamburg Open | Tier II → modern equivalent WTA 500 | Clay |
| Anna Smashnova | 6-3 6-2 | W | H2H | Match data | May 3, 2000* | R32 | Hamburg Open | Tier II → modern equivalent WTA 500 | Clay |
| Ruxandra Dragomir Ilie | 7-6(2) 3-6 3-6 | L | H2H | Match data | Apr 21, 2000* | R16 | Hilton Head | Tier I → modern equivalent WTA 1000 | Clay |
| Tara Snyder | 4-6 6-2 6-1 | W | H2H | Match data | Apr 20, 2000* | R32 | Hilton Head | Tier I → modern equivalent WTA 1000 | Clay |
| Paola Suarez | 6-2 2-6 4-6 | L | H2H | Match data | Apr 15, 2000* | QF | Amelia Island | Tier II → modern equivalent WTA 500 | Clay |
| Nicole Pratt | 6-0 7-5 | W | H2H | Match data | Apr 14, 2000* | R16 | Amelia Island | Tier II → modern equivalent WTA 500 | Clay |
| Anne Kremer | 7-5 7-6(4) | W | H2H | Match data | Apr 13, 2000* | R32 | Amelia Island | Tier II → modern equivalent WTA 500 | Clay |
| Monica Seles | 1-6 6-3 0-6 | L | H2H | Match data | Mar 24, 2000* | R16 | Miami Open | Tier I → modern equivalent WTA 1000 | Hard |
| Natasha Zvereva | 6-1 6-4 | W | H2H | Match data | Mar 23, 2000* | R32 | Miami Open | Tier I → modern equivalent WTA 1000 | Hard |
| Jennifer Hopkins | 6-2 6-4 | W | H2H | Match data | Mar 22, 2000* | R64 | Miami Open | Tier I → modern equivalent WTA 1000 | Hard |
| Nathalie Dechy | 5-7 7-5 6-7(5) | L | H2H | Match data | Mar 16, 2000* | R32 | Indian Wells Open | Tier I → modern equivalent WTA 1000 | Hard |
| Denisa Chladkova | 7-5 6-2 | W | H2H | Match data | Mar 15, 2000* | R64 | Indian Wells Open | Tier I → modern equivalent WTA 1000 | Hard |
| Lindsay Davenport | 2-6 2-6 | L | H2H | Match data | Mar 4, 2000* | SF | Scottsdale | WTA 500 | Hard |
| Ai Sugiyama | 6-4 6-2 | W | H2H | Match data | Mar 4, 2000* | QF | Scottsdale | WTA 500 | Hard |
| Sylvia Plischke | 6-1 6-1 | W | H2H | Match data | Mar 3, 2000* | R16 | Scottsdale | WTA 500 | Hard |
| Alina Jidkova | 6-2 6-1 | W | H2H | Match data | Mar 2, 2000* | R32 | Scottsdale | WTA 500 | Hard |
| Nathalie Tauziat | 6-7(6) 6-2 4-6 | L | H2H | Match data | Feb 12, 2000* | SF | Paris | Tier II → modern equivalent WTA 500 | Carpet |
| Irina Spirlea | 4-6 6-4 6-2 | W | H2H | Match data | Feb 12, 2000* | QF | Paris | Tier II → modern equivalent WTA 500 | Carpet |
| Anne Kremer | 7-6(2) 6-2 | W | H2H | Match data | Feb 11, 2000* | R16 | Paris | Tier II → modern equivalent WTA 500 | Carpet |
| Martina Hingis | 0-6 2-6 | L | H2H | Match data | Feb 5, 2000* | QF | Pan Pacific Open | Tier I → modern equivalent WTA 1000 | Carpet |
| Nicole Pratt | 6-2 1-6 6-1 | W | H2H | Match data | Feb 4, 2000* | R16 | Pan Pacific Open | Tier I → modern equivalent WTA 1000 | Carpet |
| Anne-Gaelle Sidot | 6-3 6-2 | W | H2H | Match data | Feb 3, 2000* | R32 | Pan Pacific Open | Tier I → modern equivalent WTA 1000 | Carpet |
| Lindsay Davenport | 4-6 3-6 | L | H2H | Match data | Jan 25, 2000* | R16 | Australian Open | Grand Slam | Hard |
| Kveta Peschke | 2-6 6-3 6-4 | W | H2H | Match data | Jan 23, 2000* | R32 | Australian Open | Grand Slam | Hard |
| Natasha Zvereva | 6-1 6-4 | W | H2H | Match data | Jan 20, 2000* | R64 | Australian Open | Grand Slam | Hard |
| Patricia Wartusch | 6-0 6-0 | W | H2H | Match data | Jan 19, 2000* | R128 | Australian Open | Grand Slam | Hard |
| Lindsay Davenport | 3-6 2-6 | L | H2H | Match data | Jan 12, 2000* | SF | Sydney International | Tier II → modern equivalent WTA 500 | Hard |
| Alexandra Stevenson | 4-6 6-2 6-2 | W | H2H | Match data | Jan 12, 2000* | QF | Sydney International | Tier II → modern equivalent WTA 500 | Hard |
| Jennifer Capriati | 6-4 7-5 | W | H2H | Match data | Jan 11, 2000* | R16 | Sydney International | Tier II → modern equivalent WTA 500 | Hard |
| Sabine Appelmans | 7-6(4) 6-2 | W | H2H | Match data | Jan 10, 2000* | R32 | Sydney International | Tier II → modern equivalent WTA 500 | Hard |
| Silvija Talaja | 6-4 4-6 2-6 | L | H2H | Match data | Jan 8, 2000* | QF | Gold Coast | Tier III → modern equivalent WTA 250 | Hard |
| Jana Kandarr | 6-1 (ret.) | W | H2H | Match data | Jan 7, 2000* | R16 | Gold Coast | Tier III → modern equivalent WTA 250 | Hard |
| Mary Pierce | 7-6 6-7 0-6 | L | H2H | Match data | Nov 15, 1999 | R16 | WTA Finals | WTA Finals | Carpet |
| Justine Henin | 6-7 4-6 | L | H2H | Match data | Nov 11, 1999* | R32 | Philadelphia | Tier II → modern equivalent WTA 500 | Carpet |
| Nathalie Tauziat | 6-7 5-7 | L | H2H | Match data | Nov 6, 1999* | QF | Leipzig | Tier II → modern equivalent WTA 500 | Carpet |
| Sandrine Testud | 6-2 6-4 | W | H2H | Match data | Nov 5, 1999* | R16 | Leipzig | Tier II → modern equivalent WTA 500 | Carpet |
| Anne Kremer | 7-5 6-4 | W | H2H | Match data | Nov 4, 1999* | R32 | Leipzig | Tier II → modern equivalent WTA 500 | Carpet |
| Irina Spirlea | 0-6 6-0 1-6 | L | H2H | Match data | Oct 29, 1999* | R16 | Linz Open | Tier II → modern equivalent WTA 500 | Carpet |
| Cara Black | 6-4 6-4 | W | H2H | Match data | Oct 28, 1999* | R32 | Linz Open | Tier II → modern equivalent WTA 500 | Carpet |
| Amanda Coetzer | 0-6 6-1 1-6 | L | H2H | Match data | Aug 6, 1999* | R16 | San Diego | Tier II → modern equivalent WTA 500 | Hard |
| Meilen Tu | 6-2 7-6 | W | H2H | Match data | Aug 5, 1999* | R32 | San Diego | Tier II → modern equivalent WTA 500 | Hard |
| Venus Williams | 1-6 3-6 | L | H2H | Match data | Jul 31, 1999* | QF | Stanford | Tier II → modern equivalent WTA 500 | Hard |
| Mary Joe Fernandez | 6-4 6-4 | W | H2H | Match data | Jul 30, 1999* | R16 | Stanford | Tier II → modern equivalent WTA 500 | Hard |
| Mirjana Lucic-Baroni | 6-4 6-2 | W | H2H | Match data | Jul 29, 1999* | R32 | Stanford | Tier II → modern equivalent WTA 500 | Hard |
| Venus Williams | 6-3 3-6 2-6 | L | H2H | Match data | Jun 30, 1999* | R16 | Wimbledon | Grand Slam | Grass |
| Ines Gorrochategui | 7-5 3-1 (ret.) | W | H2H | Match data | Jun 27, 1999* | R32 | Wimbledon | Grand Slam | Grass |
| Maria Vento-Kabchi | 7-5 6-4 | W | H2H | Match data | Jun 25, 1999* | R64 | Wimbledon | Grand Slam | Grass |
| Barbara Schwartz | 7-6 4-6 6-2 | W | H2H | Match data | Jun 23, 1999* | R128 | Wimbledon | Grand Slam | Grass |
| Nathalie Tauziat | 4-6 6-4 6-8 | L | H2H | Match data | Jun 19, 1999* | SF | Eastbourne Open | Tier II → modern equivalent WTA 500 | Grass |
| Nathalie Dechy | 6-3 7-6 | W | H2H | Match data | Jun 19, 1999* | QF | Eastbourne Open | Tier II → modern equivalent WTA 500 | Grass |
| Lisa Raymond | 7-6 6-4 | W | H2H | Match data | Jun 18, 1999* | R16 | Eastbourne Open | Tier II → modern equivalent WTA 500 | Grass |
| Chanda Rubin | 6-2 4-6 6-4 | W | H2H | Match data | Jun 17, 1999* | R32 | Eastbourne Open | Tier II → modern equivalent WTA 500 | Grass |
| Steffi Graf | 3-6 6-7(4) | L | H2H | Match data | Jun 1, 1999* | R16 | Roland Garros | Grand Slam | Clay |
| Patty Schnyder | 6-1 3-6 6-0 | W | H2H | Match data | May 30, 1999* | R32 | Roland Garros | Grand Slam | Clay |
| Amy Frazier | 6-4 6-1 | W | H2H | Match data | May 27, 1999* | R64 | Roland Garros | Grand Slam | Clay |
| Tamarine Tanasugarn | 6-3 6-3 | W | H2H | Match data | May 26, 1999* | R128 | Roland Garros | Grand Slam | Clay |
| Mary Joe Fernandez | 7-6 4-6 6-7 | L | H2H | Match data | May 12, 1999* | R64 | Berlin Open | Tier I → modern equivalent WTA 1000 | Clay |
| Venus Williams | 2-6 2-6 | L | H2H | Match data | May 7, 1999* | R16 | Italian Open | Tier I → modern equivalent WTA 1000 | Clay |
| Magui Serna | 6-4 6-3 | W | H2H | Match data | May 6, 1999* | R32 | Italian Open | Tier I → modern equivalent WTA 1000 | Clay |
| Rita Grande | 6-7 6-3 2-0 (ret.) | W | H2H | Match data | May 5, 1999* | R64 | Italian Open | Tier I → modern equivalent WTA 1000 | Clay |
| Ruxandra Dragomir Ilie | 3-6 5-7 | L | H2H | Match data | Apr 10, 1999* | SF | Amelia Island | Tier II → modern equivalent WTA 500 | Clay |
| Patty Schnyder | 6-0 6-2 | W | H2H | Match data | Apr 10, 1999* | QF | Amelia Island | Tier II → modern equivalent WTA 500 | Clay |
| Lindsay Davenport | 6-4 6-1 | W | H2H | Match data | Apr 9, 1999* | R16 | Amelia Island | Tier II → modern equivalent WTA 500 | Clay |
| Jennifer Capriati | 6-3 6-3 | W | H2H | Match data | Apr 8, 1999* | R32 | Amelia Island | Tier II → modern equivalent WTA 500 | Clay |
| Evgenia Kulikovskaya | 6-1 7-5 | W | H2H | Match data | Apr 7, 1999* | R64 | Amelia Island | Tier II → modern equivalent WTA 500 | Clay |
| Martina Hingis | 4-6 3-6 | L | H2H | Match data | Apr 4, 1999* | F | Hilton Head | Tier I → modern equivalent WTA 1000 | Clay |
| Patty Schnyder | 6-7 6-0 6-3 | W | H2H | Match data | Apr 3, 1999* | SF | Hilton Head | Tier I → modern equivalent WTA 1000 | Clay |
| Andrea Glass | 6-2 2-1 (ret.) | W | H2H | Match data | Apr 3, 1999* | QF | Hilton Head | Tier I → modern equivalent WTA 1000 | Clay |
| Barbara Schett | 7-6 6-4 | W | H2H | Match data | Apr 2, 1999* | R16 | Hilton Head | Tier I → modern equivalent WTA 1000 | Clay |
| María Sánchez Lorenzo | 2-6 6-3 6-1 | W | H2H | Match data | Apr 1, 1999* | R32 | Hilton Head | Tier I → modern equivalent WTA 1000 | Clay |
| Barbara Schett | 1-6 6-1 1-6 | L | H2H | Match data | Mar 22, 1999* | R16 | Key Biscayne | Tier I → modern equivalent WTA 1000 | Hard |
| Julie Halard-Decugis | 6-4 7-6 | W | H2H | Match data | Mar 21, 1999* | R32 | Key Biscayne | Tier I → modern equivalent WTA 1000 | Hard |
| Kristina Brandi | 6-7 6-0 6-2 | W | H2H | Match data | Mar 20, 1999* | R64 | Key Biscayne | Tier I → modern equivalent WTA 1000 | Hard |
| Silvia Farina Elia | 6-7 6-1 5-7 | L | H2H | Match data | Mar 10, 1999* | R64 | Indian Wells Open | Tier I → modern equivalent WTA 1000 | Hard |
| Amanda Coetzer | 4-6 2-6 | L | H2H | Match data | Feb 27, 1999* | SF | Oklahoma | Tier III → modern equivalent WTA 250 | Hard |
| Chanda Rubin | 7-5 0-6 6-3 | W | H2H | Match data | Feb 27, 1999* | QF | Oklahoma | Tier III → modern equivalent WTA 250 | Hard |
| Kristina Brandi | 6-3 6-1 | W | H2H | Match data | Feb 26, 1999* | R16 | Oklahoma | Tier III → modern equivalent WTA 250 | Hard |
| Monica Seles | 5-7 3-6 | L | H2H | Match data | Feb 6, 1999* | QF | Pan Pacific Open | Tier I → modern equivalent WTA 1000 | Carpet |
| Cara Black | 6-2 6-3 | W | H2H | Match data | Feb 5, 1999* | R16 | Pan Pacific Open | Tier I → modern equivalent WTA 1000 | Carpet |
| Anke Huber | 7-6 6-0 | W | H2H | Match data | Feb 4, 1999* | R32 | Pan Pacific Open | Tier I → modern equivalent WTA 1000 | Carpet |
Estimated from the tournament schedule where an exact match date is unavailable. Arrows show an edition's recorded category and documented modern equivalent; unresolved editions keep their recorded category. Mapping details.