| Year | Tournament | Result | Player | Age | Nation |
|---|---|---|---|---|---|
| 1999 | Wimbledon | R128 | Bohdan Ulihrach | 24 | Czech Republic |
| 1999 | Wimbledon | R128 | Albert Costa | 23 | Spain |
| 1999 | Wimbledon | R128 | Albert Portas | 25 | Spain |
| 1999 | Wimbledon | R128 | Martin Damm (born 1972) | 26 | Czech Republic |
| 1999 | Wimbledon | R128 | Michael Kohlmann | 25 | Germany |
| 1999 | Wimbledon | R128 | Guillaume Raoux | 29 | France |
| 1999 | Wimbledon | R128 | Magnus Larsson | 29 | Sweden |
| 1999 | Wimbledon | R128 | Xavier Malisse | 18 | Belgium |
| 1999 | Wimbledon | R128 | Dominik Hrbatý | 21 | Slovakia |
| 1999 | Wimbledon | R128 | Wayne Ferreira | 27 | South Africa |
| 1999 | Wimbledon | R128 | Byron Black | 29 | Zimbabwe |
| 1999 | Wimbledon | R128 | Oliver Gross | 26 | Germany |
| 1999 | Wimbledon | R128 | Vince Spadea | 24 | United States |
| 1999 | Wimbledon | R128 | Ctislav Doseděl | 28 | Czech Republic |
| 1999 | Wimbledon | R128 | Jan Siemerink | 29 | Netherlands |
| 1999 | Wimbledon | R128 | Martin Lee | 21 | United Kingdom |
| 1999 | Wimbledon | R128 | Andrei Pavel | 25 | Romania |
| 1999 | Wimbledon | R128 | Chris Wilkinson | 29 | United Kingdom |
| 1999 | Wimbledon | R128 | Juan Antonio Marín | 24 | Costa Rica |
| 1999 | Wimbledon | R128 | Dinu Pescariu | 25 | Romania |
| 1999 | Wimbledon | R128 | Jason Stoltenberg | 29 | Australia |
| 1999 | Wimbledon | R128 | Ramón Delgado | 22 | Paraguay |
| 1999 | Wimbledon | R128 | Franco Squillari | 23 | Argentina |
| 1999 | Wimbledon | R128 | Tom Spinks | 23 | United Kingdom |
| 1999 | Wimbledon | R128 | Orlin Stanoytchev | 27 | Bulgaria |
| 1999 | Wimbledon | R128 | Christian Ruud | 26 | Norway |
| 1999 | Wimbledon | R128 | Scott Draper | 25 | Australia |
| 1999 | Wimbledon | R128 | Arnaud Di Pasquale | 20 | France |
| 1999 | Wimbledon | R128 | Sargis Sargsian | 26 | Armenia |
| 1999 | Wimbledon | R128 | Cristiano Caratti | 29 | Italy |
| 1999 | Wimbledon | R128 | Paola Suárez | 22? | Argentina |
| 1999 | Wimbledon | R128 | Cătălina Cristea | 24 | Romania |
| 1999 | Wimbledon | R128 | Patty Schnyder | 20 | Switzerland |
| 1999 | Wimbledon | R128 | Anne-Gaëlle Sidot | 19 | France |
| 1999 | Wimbledon | R128 | Katarina Srebotnik | 18 | Slovenia |
| 1999 | Wimbledon | R128 | Jane Chi | 25 | United States |
| 1999 | Wimbledon | R128 | Rita Kuti-Kis | 21 | Hungary |
| 1999 | Wimbledon | R128 | Miriam Oremans | 26 | Netherlands |
| 1999 | Wimbledon | R128 | Andrea Glass | 22 | Germany |
| 1999 | Wimbledon | R128 | Émilie Loit | 20 | France |
| 1999 | Wimbledon | R128 | Åsa Svensson | 24 | Sweden |
| 1999 | Wimbledon | R128 | Adriana Serra-Zanetti | 23 | Italy |
| 1999 | Wimbledon | R128 | Samantha Smith | 27 | United Kingdom |
| 1999 | Wimbledon | R128 | Fabiola Zuluaga | 20 | Colombia |
| 1999 | Wimbledon | R128 | Jolene Watanabe | 30 | United States |
| 1999 | Wimbledon | R128 | Abigail Tordoff | 19 | United Kingdom |
| 1999 | Wimbledon | R128 | Laurence Courtois | 23 | Belgium |
| 1999 | Wimbledon | R128 | Kerry-Anne Guse | 27 | Australia |
| 1999 | Wimbledon | R128 | Kristina Brandi | 22 | Puerto Rico |
| 1999 | Wimbledon | R128 | Lilia Osterloh | 21 | United States |
Open Era Grand Slam Tennis