| Year | Tournament | Result | Player | Age | Nation |
|---|---|---|---|---|---|
| 1999 | French Open | R64 | Inés Gorrochategui | 25 | Argentina |
| 1999 | French Open | R64 | Adriana Serra-Zanetti | 23 | Italy |
| 1999 | French Open | R64 | Amy Frazier | 26 | United States |
| 1999 | French Open | R64 | Nicole Arendt | 29 | United States |
| 1999 | French Open | R64 | Ai Sugiyama | 23 | Japan |
| 1999 | French Open | R64 | Lilia Osterloh | 21 | United States |
| 1999 | French Open | R64 | Jana Nejedly | 24 | Canada |
| 1999 | French Open | R64 | Justine Henin | 16 | Belgium |
| 1999 | French Open | R64 | Lea Ghirardi | 25 | France |
| 1999 | French Open | R64 | Mary Pierce | 24 | France |
| 1999 | French Open | R64 | Emmanuelle Curutchet | 20 | France |
| 1999 | French Open | R64 | Kimberly Po | 27 | United States |
| 1999 | French Open | R64 | Kristie Boogert | 25 | Netherlands |
| 1999 | French Open | R64 | Emmanuelle Gagliardi | 22 | Switzerland |
| 1999 | French Open | R64 | Sandrine Testud | 27 | France |
| 1999 | French Open | R64 | Adriana Gerši | 22 | Czech Republic |
| 1999 | French Open | R64 | Elena Dementieva | 17 | Russia |
| 1999 | French Open | R64 | Chanda Rubin | 23 | United States |
| 1999 | French Open | R64 | Anne Kremer | 23 | Luxembourg |
| 1999 | French Open | R64 | Barbara Rittner | 26 | Germany |
| 1999 | French Open | R64 | Natasha Zvereva | 28 | Belarus |
| 1999 | French Open | R64 | Mariana Díaz Oliva | 23 | Argentina |
| 1999 | French Open | R128 | Mariano Zabaleta | 21 | Argentina |
| 1999 | French Open | R128 | Axel Pretzsch | 22 | Germany |
| 1999 | French Open | R128 | Roger Federer | 17 | Switzerland |
| 1999 | French Open | R128 | Magnus Gustafsson | 32 | Sweden |
| 1999 | French Open | R128 | Daniel Vacek | 28 | Czech Republic |
| 1999 | French Open | R128 | Galo Blanco | 22 | Spain |
| 1999 | French Open | R128 | Julien Boutter | 25 | France |
| 1999 | French Open | R128 | Jan Siemerink | 29 | Netherlands |
| 1999 | French Open | R128 | Răzvan Sabău | 21 | Romania |
| 1999 | French Open | R128 | Paul Haarhuis | 33 | Netherlands |
| 1999 | French Open | R128 | Dinu Pescariu | 25 | Romania |
| 1999 | French Open | R128 | Julian Alonso-Pintor | 21 | Spain |
| 1999 | French Open | R128 | Cecil Mamiit | 22 | Philippines |
| 1999 | French Open | R128 | Goran Ivanišević | 27 | Croatia |
| 1999 | French Open | R128 | Rainer Schüttler | 23 | Germany |
| 1999 | French Open | R128 | Lleyton Hewitt | 18 | Australia |
| 1999 | French Open | R128 | Jonas Björkman | 27 | Sweden |
| 1999 | French Open | R128 | Vladimir Voltchkov | 21 | Belarus |
| 1999 | French Open | R128 | Álex Calatrava | 25 | Spain |
| 1999 | French Open | R128 | Ramón Delgado | 22 | Paraguay |
| 1999 | French Open | R128 | Wayne Black | 25 | Zimbabwe |
| 1999 | French Open | R128 | Mark Philippoussis | 22 | Australia |
| 1999 | French Open | R128 | Adrian Voinea | 24 | Romania |
| 1999 | French Open | R128 | Ján Krošlák | 24 | Slovakia |
| 1999 | French Open | R128 | Hector Moretti | 26 | Argentina |
| 1999 | French Open | R128 | Lionel Roux | 26 | France |
| 1999 | French Open | R128 | Carlos Costa | 31 | Spain |
| 1999 | French Open | R128 | Christophe Rochus | 20 | Belgium |
Open Era Grand Slam Tennis