| Year | Tournament | Result | Player | Age | Nation |
|---|---|---|---|---|---|
| 1999 | US Open | R128 | Bernd Karbacher | 31 | Germany |
| 1999 | US Open | R128 | Jacobo Díaz | 23 | Spain |
| 1999 | US Open | R128 | Thomas Enqvist | 25 | Sweden |
| 1999 | US Open | R128 | Felix Mantilla | 24 | Spain |
| 1999 | US Open | R128 | Wayne Ferreira | 27 | South Africa |
| 1999 | US Open | R128 | Mariano Zabaleta | 21 | Argentina |
| 1999 | US Open | R128 | Albert Portas | 25 | Spain |
| 1999 | US Open | R128 | Bob Bryan | 21 | United States |
| 1999 | US Open | R128 | Sargis Sargsian | 26 | Armenia |
| 1999 | US Open | R128 | Jeff Tarango | 30 | United States |
| 1999 | US Open | R128 | Andrew Ilie | 23 | Australia |
| 1999 | US Open | R128 | Gastón Gaudio | 20 | Argentina |
| 1999 | US Open | R128 | Byron Black | 29 | Zimbabwe |
| 1999 | US Open | R128 | Martin Rodriguez | 29 | Argentina |
| 1999 | US Open | R128 | Marc Rosset | 28 | Switzerland |
| 1999 | US Open | R128 | Àlex Corretja | 25 | Spain |
| 1999 | US Open | R128 | Takao Suzuki | 22 | Japan |
| 1999 | US Open | R128 | Stéphane Huet | 28 | France |
| 1999 | US Open | R128 | Pat Rafter | 26 | Australia |
| 1999 | US Open | R128 | Phillip King | 17 | United States |
| 1999 | US Open | R128 | Sjeng Schalken | 22 | Netherlands |
| 1999 | US Open | R128 | Jeff Morrison | 20 | United States |
| 1999 | US Open | R128 | Jan Siemerink | 29 | Netherlands |
| 1999 | US Open | R128 | Nicklas Kulti | 28 | Sweden |
| 1999 | US Open | R128 | Anne Miller | 22 | United States |
| 1999 | US Open | R128 | Laura Golarsa | 31 | Italy |
| 1999 | US Open | R128 | Lenka Němečková | 23 | Czech Republic |
| 1999 | US Open | R128 | Inés Gorrochategui | 26 | Argentina |
| 1999 | US Open | R128 | Rita Kuti-Kis | 21 | Hungary |
| 1999 | US Open | R128 | Elena Tatarkova | 23 | Ukraine |
| 1999 | US Open | R128 | Lilia Osterloh | 21 | United States |
| 1999 | US Open | R128 | Anna Smashnova | 23 | Israel |
| 1999 | US Open | R128 | Alicia Molik | 18 | Australia |
| 1999 | US Open | R128 | María Vento-Kabchi | 25 | Venezuela |
| 1999 | US Open | R128 | Barbara Rittner | 26 | Germany |
| 1999 | US Open | R128 | Pavlina Nola | 25 | Bulgaria |
| 1999 | US Open | R128 | Sandra Načuk | 19 | Yugoslavia |
| 1999 | US Open | R128 | Brie Rippner | 19 | United States |
| 1999 | US Open | R128 | Cara Black | 20 | Zimbabwe |
| 1999 | US Open | R128 | Marlene Weingärtner | 19 | Germany |
| 1999 | US Open | R128 | Olga Barabanschikova | 19 | Belarus |
| 1999 | US Open | R128 | Els Callens | 29 | Belgium |
| 1999 | US Open | R128 | Melissa Middleton | 17 | United States |
| 1999 | US Open | R128 | Jana Kandarr | 22 | Germany |
| 1999 | US Open | R128 | Kimberly Po | 27 | United States |
| 1999 | US Open | R128 | Iva Majoli | 22 | Croatia |
| 1999 | US Open | R128 | Ľudmila Cervanová | 19 | Slovakia |
| 1999 | US Open | R128 | Jana Nejedly | 25 | Canada |
| 1999 | US Open | R128 | Lubomira Bacheva | 24 | Bulgaria |
| 1999 | US Open | R128 | Laurence Courtois | 23 | Belgium |
Open Era Grand Slam Tennis