| Year | Tournament | Result | Player | Age | Nation |
|---|---|---|---|---|---|
| 1999 | US Open | R16 | Arnaud Clément | 21 | France |
| 1999 | US Open | R16 | Marcelo Ríos | 23 | Chile |
| 1999 | US Open | R16 | Magnus Norman | 23 | Sweden |
| 1999 | US Open | R16 | Greg Rusedski | 26 | United Kingdom |
| 1999 | US Open | R16 | Jiří Novák | 24 | Czech Republic |
| 1999 | US Open | R16 | Andriy Medvedev | 25 | Ukraine |
| 1999 | US Open | R16 | Elena Likhovtseva | 23 | Russia |
| 1999 | US Open | R16 | Mary Joe Fernández | 28 | United States |
| 1999 | US Open | R16 | Conchita Martínez | 27 | Spain |
| 1999 | US Open | R16 | Jennifer Capriati | 23 | United States |
| 1999 | US Open | R16 | Amélie Mauresmo | 20 | France |
| 1999 | US Open | R16 | Sabine Appelmans | 27 | Belgium |
| 1999 | US Open | R16 | Julie Halard-Decugis | 28 | France |
| 1999 | US Open | R16 | Arantxa Sánchez Vicario | 27 | Spain |
| 1999 | US Open | R32 | Hicham Arazi | 25 | Morocco |
| 1999 | US Open | R32 | Jonas Björkman | 27 | Sweden |
| 1999 | US Open | R32 | Peter Wessels | 21 | Netherlands |
| 1999 | US Open | R32 | Goran Ivanišević | 27 | Croatia |
| 1999 | US Open | R32 | John van Lottum | 23 | Netherlands |
| 1999 | US Open | R32 | Lleyton Hewitt | 18 | Australia |
| 1999 | US Open | R32 | Laurence Tieleman | 26 | Italy |
| 1999 | US Open | R32 | Magnus Larsson | 29 | Sweden |
| 1999 | US Open | R32 | Richard Fromberg | 29 | Australia |
| 1999 | US Open | R32 | Nicolas Kiefer | 22 | Germany |
| 1999 | US Open | R32 | Justin Gimelstob | 22 | United States |
| 1999 | US Open | R32 | Chris Woodruff | 26 | United States |
| 1999 | US Open | R32 | Xavier Malisse | 19 | Belgium |
| 1999 | US Open | R32 | Fabrice Santoro | 26 | France |
| 1999 | US Open | R32 | Ján Krošlák | 24 | Slovakia |
| 1999 | US Open | R32 | Fredrik Jonsson | 22 | Sweden |
| 1999 | US Open | R32 | Magüi Serna | 20 | Spain |
| 1999 | US Open | R32 | Virginia Ruano Pascual | 25 | Spain |
| 1999 | US Open | R32 | Henrieta Nagyová | 20 | Slovakia |
| 1999 | US Open | R32 | Ángeles Montolio | 24 | Spain |
| 1999 | US Open | R32 | Jana Novotná | 30 | Czech Republic |
| 1999 | US Open | R32 | Irina Spîrlea | 25 | Romania |
| 1999 | US Open | R32 | Dominique Monami | 26 | Belgium |
| 1999 | US Open | R32 | Amy Frazier | 26 | United States |
| 1999 | US Open | R32 | Sandra Klösel | 20 | Germany |
| 1999 | US Open | R32 | Nathalie Tauziat | 31 | France |
| 1999 | US Open | R32 | Patty Schnyder | 20 | Switzerland |
| 1999 | US Open | R32 | Amélie Cocheteux | 21 | France |
| 1999 | US Open | R32 | Kim Clijsters | 16 | Belgium |
| 1999 | US Open | R32 | Ai Sugiyama | 24 | Japan |
| 1999 | US Open | R32 | Elena Dementieva | 17 | Russia |
| 1999 | US Open | R32 | Tara Snyder | 22 | United States |
| 1999 | US Open | R64 | Axel Pretzsch | 23 | Germany |
| 1999 | US Open | R64 | Cristiano Caratti | 29 | Italy |
| 1999 | US Open | R64 | Daniel Vacek | 28 | Czech Republic |
| 1999 | US Open | R64 | Paul Haarhuis | 33 | Netherlands |
Open Era Grand Slam Tennis