| Year | Tournament | Result | Player | Age | Nation |
|---|---|---|---|---|---|
| 1999 | Wimbledon | R32 | Corina Morariu | 21 | United States |
| 1999 | Wimbledon | R32 | Amanda Coetzer | 27 | South Africa |
| 1999 | Wimbledon | R64 | Nicolás Lapentti | 22 | Ecuador |
| 1999 | Wimbledon | R64 | Sandon Stolle | 28 | Australia |
| 1999 | Wimbledon | R64 | Jamie Delgado | 22 | United Kingdom |
| 1999 | Wimbledon | R64 | Chris Woodruff | 26 | United States |
| 1999 | Wimbledon | R64 | Fernando Vicente | 22 | Spain |
| 1999 | Wimbledon | R64 | Todd Woodbridge | 28 | Australia |
| 1999 | Wimbledon | R64 | Marc Rosset | 28 | Switzerland |
| 1999 | Wimbledon | R64 | Arvind Parmar | 21 | United Kingdom |
| 1999 | Wimbledon | R64 | Jan-Michael Gambill | 22 | United States |
| 1999 | Wimbledon | R64 | Jiří Novák | 24 | Czech Republic |
| 1999 | Wimbledon | R64 | Jeff Tarango | 30 | United States |
| 1999 | Wimbledon | R64 | Andriy Medvedev | 24 | Ukraine |
| 1999 | Wimbledon | R64 | David Prinosil | 26 | Germany |
| 1999 | Wimbledon | R64 | Mark Woodforde | 33 | Australia |
| 1999 | Wimbledon | R64 | Felix Mantilla | 24 | Spain |
| 1999 | Wimbledon | R64 | Guillermo Cañas | 21 | Argentina |
| 1999 | Wimbledon | R64 | Richard Fromberg | 29 | Australia |
| 1999 | Wimbledon | R64 | Younes El Aynaoui | 27 | Morocco |
| 1999 | Wimbledon | R64 | Andrew Ilie | 23 | Australia |
| 1999 | Wimbledon | R64 | Galo Blanco | 22 | Spain |
| 1999 | Wimbledon | R64 | Rainer Schüttler | 23 | Germany |
| 1999 | Wimbledon | R64 | Sébastien Lareau | 25 | Canada |
| 1999 | Wimbledon | R64 | Nicolas Kiefer | 21 | Germany |
| 1999 | Wimbledon | R64 | Jonas Björkman | 27 | Sweden |
| 1999 | Wimbledon | R64 | Carlos Moyá | 22 | Spain |
| 1999 | Wimbledon | R64 | Fabrice Santoro | 26 | France |
| 1999 | Wimbledon | R64 | Thomas Johansson | 24 | Sweden |
| 1999 | Wimbledon | R64 | André Sá | 22 | Brazil |
| 1999 | Wimbledon | R64 | Arnaud Clément | 21 | France |
| 1999 | Wimbledon | R64 | Karim Alami | 26 | Morocco |
| 1999 | Wimbledon | R64 | Gianluca Pozzi | 34 | Italy |
| 1999 | Wimbledon | R64 | Paradorn Srichaphan | 20 | Thailand |
| 1999 | Wimbledon | R64 | Mariaan de Swardt | 28 | South Africa |
| 1999 | Wimbledon | R64 | Nadia Petrova | 17 | Russia |
| 1999 | Wimbledon | R64 | Sylvia Plischke | 21 | Austria |
| 1999 | Wimbledon | R64 | Amanda Hopmans | 23 | Netherlands |
| 1999 | Wimbledon | R64 | Jennifer Capriati | 23 | United States |
| 1999 | Wimbledon | R64 | Ai Sugiyama | 23 | Japan |
| 1999 | Wimbledon | R64 | Janet Lee | 22 | Taiwan |
| 1999 | Wimbledon | R64 | Karen Cross | 25 | United Kingdom |
| 1999 | Wimbledon | R64 | Kristie Boogert | 25 | Netherlands |
| 1999 | Wimbledon | R64 | Elena Tatarkova | 22 | Ukraine |
| 1999 | Wimbledon | R64 | Miho Saeki | 23 | Japan |
| 1999 | Wimbledon | R64 | María Vento-Kabchi | 25 | Venezuela |
| 1999 | Wimbledon | R64 | Barbara Rittner | 26 | Germany |
| 1999 | Wimbledon | R64 | Maureen Drake | 28 | Canada |
| 1999 | Wimbledon | R64 | Mariana Díaz Oliva | 23 | Argentina |
| 1999 | Wimbledon | R64 | Marlene Weingärtner | 19 | Germany |
Open Era Grand Slam Tennis