| Year | Tournament | Result | Player | Age | Nation |
|---|---|---|---|---|---|
| 1999 | French Open | S | Monica Seles | 25 | United States |
| 1999 | French Open | S | Arantxa Sánchez Vicario | 27 | Spain |
| 1999 | French Open | Q | Gustavo Kuerten | 22 | Brazil |
| 1999 | French Open | Q | Marcelo Ríos | 23 | Chile |
| 1999 | French Open | Q | Àlex Corretja | 25 | Spain |
| 1999 | French Open | Q | Marcelo Filippini | 31 | Uruguay |
| 1999 | French Open | Q | Barbara Schwartz | 20 | Austria |
| 1999 | French Open | Q | Lindsay Davenport | 22 | United States |
| 1999 | French Open | Q | Sylvia Plischke | 21 | Austria |
| 1999 | French Open | Q | Conchita Martínez | 27 | Spain |
| 1999 | French Open | R16 | Felix Mantilla | 24 | Spain |
| 1999 | French Open | R16 | Greg Rusedski | 25 | United Kingdom |
| 1999 | French Open | R16 | Stefan Koubek | 22 | Austria |
| 1999 | French Open | R16 | Marat Safin | 19 | Russia |
| 1999 | French Open | R16 | Alberto Berasategui | 25 | Spain |
| 1999 | French Open | R16 | Bohdan Ulihrach | 24 | Czech Republic |
| 1999 | French Open | R16 | Arnaud Di Pasquale | 20 | France |
| 1999 | French Open | R16 | Carlos Moyá | 22 | Spain |
| 1999 | French Open | R16 | Gala León García | 25 | Spain |
| 1999 | French Open | R16 | Julie Halard-Decugis | 28 | France |
| 1999 | French Open | R16 | Jana Novotná | 30 | Czech Republic |
| 1999 | French Open | R16 | Venus Williams | 18 | United States |
| 1999 | French Open | R16 | Mary Joe Fernández | 27 | United States |
| 1999 | French Open | R16 | Anna Kournikova | 17 | Russia |
| 1999 | French Open | R16 | Ruxandra Dragomir | 26 | Romania |
| 1999 | French Open | R16 | Jennifer Capriati | 23 | United States |
| 1999 | French Open | R32 | Davide Sanguinetti | 26 | Italy |
| 1999 | French Open | R32 | Tommy Haas | 21 | Germany |
| 1999 | French Open | R32 | Gastón Gaudio | 20 | Argentina |
| 1999 | French Open | R32 | Tim Henman | 24 | United Kingdom |
| 1999 | French Open | R32 | Vince Spadea | 24 | United States |
| 1999 | French Open | R32 | Chris Woodruff | 26 | United States |
| 1999 | French Open | R32 | Sargis Sargsian | 25 | Armenia |
| 1999 | French Open | R32 | Sébastien Grosjean | 21 | France |
| 1999 | French Open | R32 | Pat Rafter | 26 | Australia |
| 1999 | French Open | R32 | Albert Costa | 23 | Spain |
| 1999 | French Open | R32 | Christian Ruud | 26 | Norway |
| 1999 | French Open | R32 | Andrew Ilie | 23 | Australia |
| 1999 | French Open | R32 | Sjeng Schalken | 22 | Netherlands |
| 1999 | French Open | R32 | Andrea Gaudenzi | 25 | Italy |
| 1999 | French Open | R32 | Hicham Arazi | 25 | Morocco |
| 1999 | French Open | R32 | Byron Black | 29 | Zimbabwe |
| 1999 | French Open | R32 | Barbara Schett | 23 | Austria |
| 1999 | French Open | R32 | Patty Schnyder | 20 | Switzerland |
| 1999 | French Open | R32 | Květa Peschke | 23 | Czech Republic |
| 1999 | French Open | R32 | Serena Williams | 17 | United States |
| 1999 | French Open | R32 | Fabiola Zuluaga | 20 | Colombia |
| 1999 | French Open | R32 | Elena Likhovtseva | 23 | Russia |
| 1999 | French Open | R32 | Cristina Torrens-Valero | 24 | Spain |
| 1999 | French Open | R32 | Irina Spîrlea | 25 | Romania |
Open Era Grand Slam Tennis