| Year | Tournament | Result | Player | Age | Nation |
|---|---|---|---|---|---|
| 1999 | Australian Open | R32 | Nicole Pratt | 25 | Australia |
| 1999 | Australian Open | R32 | Jana Novotná | 30 | Czech Republic |
| 1999 | Australian Open | R32 | Rita Grande | 23 | Italy |
| 1999 | Australian Open | R32 | Jana Nejedly | 24 | Canada |
| 1999 | Australian Open | R32 | Andrea Glass | 22 | Germany |
| 1999 | Australian Open | R32 | Conchita Martínez | 26 | Spain |
| 1999 | Australian Open | R32 | Ruxandra Dragomir | 26 | Romania |
| 1999 | Australian Open | R32 | Serena Williams | 17 | United States |
| 1999 | Australian Open | R32 | Natasha Zvereva | 27 | Belarus |
| 1999 | Australian Open | R32 | Mary Joe Fernández | 27 | United States |
| 1999 | Australian Open | R32 | Jelena Dokic | 15 | Australia |
| 1999 | Australian Open | R32 | Elena Likhovtseva | 23 | Russia |
| 1999 | Australian Open | R32 | Sylvia Plischke | 21 | Austria |
| 1999 | Australian Open | R32 | Sabine Appelmans | 26 | Belgium |
| 1999 | Australian Open | R64 | Andrei Cherkasov | 28 | Russia |
| 1999 | Australian Open | R64 | Gustavo Kuerten | 22 | Brazil |
| 1999 | Australian Open | R64 | Arnaud Clément | 21 | France |
| 1999 | Australian Open | R64 | Byron Black | 29 | Zimbabwe |
| 1999 | Australian Open | R64 | Mariano Zabaleta | 20 | Argentina |
| 1999 | Australian Open | R64 | Ctislav Doseděl | 28 | Czech Republic |
| 1999 | Australian Open | R64 | Daniel Vacek | 27 | Czech Republic |
| 1999 | Australian Open | R64 | Sandon Stolle | 28 | Australia |
| 1999 | Australian Open | R64 | Jens Knippschild | 23 | Germany |
| 1999 | Australian Open | R64 | Andriy Medvedev | 24 | Ukraine |
| 1999 | Australian Open | R64 | Paul Haarhuis | 32 | Netherlands |
| 1999 | Australian Open | R64 | Jason Stoltenberg | 28 | Australia |
| 1999 | Australian Open | R64 | Davide Sanguinetti | 26 | Italy |
| 1999 | Australian Open | R64 | Julian Alonso-Pintor | 21 | Spain |
| 1999 | Australian Open | R64 | Greg Rusedski | 25 | United Kingdom |
| 1999 | Australian Open | R64 | Mark Woodforde | 33 | Australia |
| 1999 | Australian Open | R64 | Michael Chang | 26 | United States |
| 1999 | Australian Open | R64 | Hendrik Dreekmann | 23 | Germany |
| 1999 | Australian Open | R64 | Franco Squillari | 23 | Argentina |
| 1999 | Australian Open | R64 | Mariano Puerta | 20 | Argentina |
| 1999 | Australian Open | R64 | Younes El Aynaoui | 27 | Morocco |
| 1999 | Australian Open | R64 | Cecil Mamiit | 22 | Philippines |
| 1999 | Australian Open | R64 | Stéphane Huet | 27 | France |
| 1999 | Australian Open | R64 | Lionel Roux | 25 | France |
| 1999 | Australian Open | R64 | Sjeng Schalken | 22 | Netherlands |
| 1999 | Australian Open | R64 | Justin Gimelstob | 21 | United States |
| 1999 | Australian Open | R64 | Jérôme Golmard | 25 | France |
| 1999 | Australian Open | R64 | Guillaume Raoux | 28 | France |
| 1999 | Australian Open | R64 | Lleyton Hewitt | 17 | Australia |
| 1999 | Australian Open | R64 | Àlex Corretja | 24 | Spain |
| 1999 | Australian Open | R64 | Magnus Norman | 22 | Sweden |
| 1999 | Australian Open | R64 | Sargis Sargsian | 25 | Armenia |
| 1999 | Australian Open | R64 | Brie Rippner | 19 | United States |
| 1999 | Australian Open | R64 | Anna Smashnova | 22 | Israel |
| 1999 | Australian Open | R64 | Virginia Ruano Pascual | 25 | Spain |
| 1999 | Australian Open | R64 | Barbara Schwartz | 19 | Austria |
Open Era Grand Slam Tennis