| Year | Tournament | Result | Player | Age | Nation |
|---|---|---|---|---|---|
| 1999 | Wimbledon | Q | Jelena Dokic | 16 | Australia |
| 1999 | Wimbledon | Q | Venus Williams | 19 | United States |
| 1999 | Wimbledon | Q | Jana Novotná | 30 | Czech Republic |
| 1999 | Wimbledon | Q | Nathalie Tauziat | 31 | France |
| 1999 | Wimbledon | R16 | Daniel Nestor | 26 | Canada |
| 1999 | Wimbledon | R16 | Greg Rusedski | 25 | United Kingdom |
| 1999 | Wimbledon | R16 | Karol Kučera | 25 | Slovakia |
| 1999 | Wimbledon | R16 | Jim Courier | 28 | United States |
| 1999 | Wimbledon | R16 | Lorenzo Manta | 24 | Switzerland |
| 1999 | Wimbledon | R16 | Boris Becker | 31 | Germany |
| 1999 | Wimbledon | R16 | Goran Ivanišević | 27 | Croatia |
| 1999 | Wimbledon | R16 | Wayne Arthurs | 28 | Australia |
| 1999 | Wimbledon | R16 | Lisa Raymond | 25 | United States |
| 1999 | Wimbledon | R16 | Dominique Monami | 26 | Belgium |
| 1999 | Wimbledon | R16 | Nathalie Dechy | 20 | France |
| 1999 | Wimbledon | R16 | Tamarine Tanasugarn | 22 | Thailand |
| 1999 | Wimbledon | R16 | Anna Kournikova | 18 | Russia |
| 1999 | Wimbledon | R16 | Kim Clijsters | 16 | Belgium |
| 1999 | Wimbledon | R16 | Barbara Schett | 23 | Austria |
| 1999 | Wimbledon | R16 | Mary Pierce | 24 | France |
| 1999 | Wimbledon | R32 | Nenad Zimonjić | 23 | Serbia |
| 1999 | Wimbledon | R32 | Yevgeny Kafelnikov | 25 | Russia |
| 1999 | Wimbledon | R32 | Jens Knippschild | 24 | Germany |
| 1999 | Wimbledon | R32 | Sébastien Grosjean | 21 | France |
| 1999 | Wimbledon | R32 | Sjeng Schalken | 22 | Netherlands |
| 1999 | Wimbledon | R32 | Tommy Haas | 21 | Germany |
| 1999 | Wimbledon | R32 | Lleyton Hewitt | 18 | Australia |
| 1999 | Wimbledon | R32 | Paul Haarhuis | 33 | Netherlands |
| 1999 | Wimbledon | R32 | Thomas Enqvist | 25 | Sweden |
| 1999 | Wimbledon | R32 | Daniel Vacek | 28 | Czech Republic |
| 1999 | Wimbledon | R32 | Alberto Martín | 20 | Spain |
| 1999 | Wimbledon | R32 | Richard Krajicek | 27 | Netherlands |
| 1999 | Wimbledon | R32 | Francisco Clavet | 30 | Spain |
| 1999 | Wimbledon | R32 | Paul Goldstein | 22 | United States |
| 1999 | Wimbledon | R32 | Danny Sapsford | 30 | United Kingdom |
| 1999 | Wimbledon | R32 | Magnus Norman | 23 | Sweden |
| 1999 | Wimbledon | R32 | Larisa Neiland | 32 | Latvia |
| 1999 | Wimbledon | R32 | Elena Likhovtseva | 23 | Russia |
| 1999 | Wimbledon | R32 | Conchita Martínez | 27 | Spain |
| 1999 | Wimbledon | R32 | Anne Kremer | 23 | Luxembourg |
| 1999 | Wimbledon | R32 | Sandrine Testud | 27 | France |
| 1999 | Wimbledon | R32 | Laura Golarsa | 31 | Italy |
| 1999 | Wimbledon | R32 | María Sánchez Lorenzo | 21 | Spain |
| 1999 | Wimbledon | R32 | Tatiana Panova | 22 | Russia |
| 1999 | Wimbledon | R32 | Seda Noorlander | 25 | Netherlands |
| 1999 | Wimbledon | R32 | Monica Seles | 25 | United States |
| 1999 | Wimbledon | R32 | Sarah Pitkowski-Malcor | 23 | France |
| 1999 | Wimbledon | R32 | Julie Halard-Decugis | 28 | France |
| 1999 | Wimbledon | R32 | Elena Pampoulova | 27 | Germany |
| 1999 | Wimbledon | R32 | Inés Gorrochategui | 26 | Argentina |
Open Era Grand Slam Tennis