| Year | Tournament | Result | Player | Age | Nation |
|---|---|---|---|---|---|
| 1999 | US Open | R64 | Guillermo Cañas | 21 | Argentina |
| 1999 | US Open | R64 | Michael Chang | 27 | United States |
| 1999 | US Open | R64 | Galo Blanco | 22 | Spain |
| 1999 | US Open | R64 | Max Mirnyi | 22 | Belarus |
| 1999 | US Open | R64 | Michael Kohlmann | 25 | Germany |
| 1999 | US Open | R64 | Markus Hipfl | 21 | Austria |
| 1999 | US Open | R64 | Ivan Ljubičić | 20 | Bosnia and Herzegovina |
| 1999 | US Open | R64 | Lorenzo Manta | 24 | Switzerland |
| 1999 | US Open | R64 | Paul Goldstein | 23 | United States |
| 1999 | US Open | R64 | Wayne Arthurs | 28 | Australia |
| 1999 | US Open | R64 | Cecil Mamiit | 23 | Philippines |
| 1999 | US Open | R64 | Sébastien Lareau | 25 | Canada |
| 1999 | US Open | R64 | Carlos Moyá | 23 | Spain |
| 1999 | US Open | R64 | Kenneth Carlsen | 26 | Denmark |
| 1999 | US Open | R64 | George Bastl | 24 | Switzerland |
| 1999 | US Open | R64 | Marat Safin | 19 | Russia |
| 1999 | US Open | R64 | Younes El Aynaoui | 27 | Morocco |
| 1999 | US Open | R64 | Mariano Puerta | 20 | Argentina |
| 1999 | US Open | R64 | Lars Burgsmüller | 23 | Germany |
| 1999 | US Open | R64 | Fernando Meligeni | 28 | Brazil |
| 1999 | US Open | R64 | Fernando Vicente | 22 | Spain |
| 1999 | US Open | R64 | David Prinosil | 26 | Germany |
| 1999 | US Open | R64 | Nicolás Lapentti | 23 | Ecuador |
| 1999 | US Open | R64 | Mark Woodforde | 33 | Australia |
| 1999 | US Open | R64 | Richey Reneberg | 33 | United States |
| 1999 | US Open | R64 | Jan-Michael Gambill | 22 | United States |
| 1999 | US Open | R64 | Christian Ruud | 27 | Norway |
| 1999 | US Open | R64 | Gianluca Pozzi | 34 | Italy |
| 1999 | US Open | R64 | Paola Suárez | 23 | Argentina |
| 1999 | US Open | R64 | Samantha Reeves | 20 | United States |
| 1999 | US Open | R64 | María Sánchez Lorenzo | 21 | Spain |
| 1999 | US Open | R64 | Åsa Svensson | 24 | Sweden |
| 1999 | US Open | R64 | Amanda Hopmans | 23 | Netherlands |
| 1999 | US Open | R64 | Jelena Kostanić Tošić | 18 | Croatia |
| 1999 | US Open | R64 | Karina Habšudová | 26 | Slovakia |
| 1999 | US Open | R64 | Alexia Dechaume-Balleret | 29 | France |
| 1999 | US Open | R64 | Fabiola Zuluaga | 20 | Colombia |
| 1999 | US Open | R64 | Tina Pisnik | 18 | Slovenia |
| 1999 | US Open | R64 | Tamarine Tanasugarn | 22 | Thailand |
| 1999 | US Open | R64 | Gala León García | 25 | Spain |
| 1999 | US Open | R64 | Silvia Farina Elia | 27 | Italy |
| 1999 | US Open | R64 | Adriana Gerši | 23 | Czech Republic |
| 1999 | US Open | R64 | Sarah Pitkowski-Malcor | 23 | France |
| 1999 | US Open | R64 | Seda Noorlander | 25 | Netherlands |
| 1999 | US Open | R64 | Sylvia Plischke | 22 | Austria |
| 1999 | US Open | R64 | Mariaan de Swardt | 28 | South Africa |
| 1999 | US Open | R64 | Natasha Zvereva | 28 | Belarus |
| 1999 | US Open | R64 | Rita Grande | 24 | Italy |
| 1999 | US Open | R64 | Nicole Pratt | 26 | Australia |
| 1999 | US Open | R64 | Anne Kremer | 23 | Luxembourg |
Open Era Grand Slam Tennis