| Year | Tournament | Result | Player | Age | Nation |
|---|---|---|---|---|---|
| 1999 | French Open | R32 | Anna Smashnova | 22 | Israel |
| 1999 | French Open | R32 | Alicia Molik | 18 | Australia |
| 1999 | French Open | R32 | Nathalie Dechy | 20 | France |
| 1999 | French Open | R32 | Mariaan de Swardt | 28 | South Africa |
| 1999 | French Open | R32 | Åsa Svensson | 23 | Sweden |
| 1999 | French Open | R32 | Silvija Talaja | 21 | Croatia |
| 1999 | French Open | R32 | Silvia Farina Elia | 27 | Italy |
| 1999 | French Open | R32 | María Sánchez Lorenzo | 21 | Spain |
| 1999 | French Open | R64 | Pete Sampras | 27 | United States |
| 1999 | French Open | R64 | Martin Damm (born 1972) | 26 | Czech Republic |
| 1999 | French Open | R64 | Albert Portas | 25 | Spain |
| 1999 | French Open | R64 | Richard Krajicek | 27 | Netherlands |
| 1999 | French Open | R64 | Fernando Vicente | 22 | Spain |
| 1999 | French Open | R64 | Bernd Karbacher | 31 | Germany |
| 1999 | French Open | R64 | Max Mirnyi | 21 | Belarus |
| 1999 | French Open | R64 | Alex Moron | 28 | Spain |
| 1999 | French Open | R64 | Thomas Enqvist | 25 | Sweden |
| 1999 | French Open | R64 | Nicolas Escudé | 23 | France |
| 1999 | French Open | R64 | Jason Stoltenberg | 29 | Australia |
| 1999 | French Open | R64 | Magnus Larsson | 29 | Sweden |
| 1999 | French Open | R64 | Markus Hantschk | 21 | Germany |
| 1999 | French Open | R64 | Francisco Clavet | 30 | Spain |
| 1999 | French Open | R64 | Mariano Puerta | 20 | Argentina |
| 1999 | French Open | R64 | Guillermo Cañas | 21 | Argentina |
| 1999 | French Open | R64 | Mosé Navarra | 24 | Italy |
| 1999 | French Open | R64 | Younes El Aynaoui | 27 | Morocco |
| 1999 | French Open | R64 | Hernán Gumy | 27 | Argentina |
| 1999 | French Open | R64 | Yevgeny Kafelnikov | 25 | Russia |
| 1999 | French Open | R64 | Stéphane Huet | 28 | France |
| 1999 | French Open | R64 | Arnaud Clément | 21 | France |
| 1999 | French Open | R64 | Jiří Novák | 24 | Czech Republic |
| 1999 | French Open | R64 | Agustín Calleri | 22 | Argentina |
| 1999 | French Open | R64 | Arnaud Boetsch | 30 | France |
| 1999 | French Open | R64 | Petr Korda | 31 | Czech Republic |
| 1999 | French Open | R64 | Wayne Ferreira | 27 | South Africa |
| 1999 | French Open | R64 | Nicolás Lapentti | 22 | Ecuador |
| 1999 | French Open | R64 | Jens Knippschild | 24 | Germany |
| 1999 | French Open | R64 | Jim Courier | 28 | United States |
| 1999 | French Open | R64 | Martin Rodriguez | 29 | Argentina |
| 1999 | French Open | R64 | Richard Fromberg | 29 | Australia |
| 1999 | French Open | R64 | Els Callens | 28 | Belgium |
| 1999 | French Open | R64 | Paola Suárez | 22 | Argentina |
| 1999 | French Open | R64 | Katarina Srebotnik | 18 | Slovenia |
| 1999 | French Open | R64 | Olga Barabanschikova | 19 | Belarus |
| 1999 | French Open | R64 | Amélie Mauresmo | 19 | France |
| 1999 | French Open | R64 | Nathalie Tauziat | 31 | France |
| 1999 | French Open | R64 | Elena Pampoulova | 27 | Germany |
| 1999 | French Open | R64 | Andrea Glass | 22 | Germany |
| 1999 | French Open | R64 | Raluca Sandu | 19 | Romania |
| 1999 | French Open | R64 | Lubomira Bacheva | 24 | Bulgaria |
Open Era Grand Slam Tennis