| Year | Tournament | Result | Player | Age | Nation |
|---|---|---|---|---|---|
| 1999 | French Open | R128 | Franco Squillari | 23 | Argentina |
| 1999 | French Open | R128 | Nicolas Kiefer | 21 | Germany |
| 1999 | French Open | R128 | Cédric Pioline | 29 | France |
| 1999 | French Open | R128 | Mark Woodforde | 33 | Australia |
| 1999 | French Open | R128 | Jan-Michael Gambill | 21 | United States |
| 1999 | French Open | R128 | Michael Chang | 27 | United States |
| 1999 | French Open | R128 | Germán Puentes | 26 | Spain |
| 1999 | French Open | R128 | Diego Moyano | 24 | Argentina |
| 1999 | French Open | R128 | Jeff Tarango | 30 | United States |
| 1999 | French Open | R128 | Thomas Muster | 31 | Austria |
| 1999 | French Open | R128 | Magnus Norman | 22 | Sweden |
| 1999 | French Open | R128 | Jean-René Lisnard | 19 | France |
| 1999 | French Open | R128 | Xavier Malisse | 18 | Belgium |
| 1999 | French Open | R128 | Karim Alami | 26 | Morocco |
| 1999 | French Open | R128 | John van Lottum | 23 | Netherlands |
| 1999 | French Open | R128 | Justin Gimelstob | 22 | United States |
| 1999 | French Open | R128 | Scott Draper | 24 | Australia |
| 1999 | French Open | R128 | Marc Rosset | 28 | Switzerland |
| 1999 | French Open | R128 | Daniel Nestor | 26 | Canada |
| 1999 | French Open | R128 | Gianluca Pozzi | 33 | Italy |
| 1999 | French Open | R128 | Rodolphe Gilbert | 30 | France |
| 1999 | French Open | R128 | Guillaume Raoux | 29 | France |
| 1999 | French Open | R128 | Markus Hipfl | 21 | Austria |
| 1999 | French Open | R128 | Karol Kučera | 25 | Slovakia |
| 1999 | French Open | R128 | Alberto Martín | 20 | Spain |
| 1999 | French Open | R128 | Fabrice Santoro | 26 | France |
| 1999 | French Open | R128 | Todd Woodbridge | 28 | Australia |
| 1999 | French Open | R128 | Kenneth Carlsen | 26 | Denmark |
| 1999 | French Open | R128 | Juan Antonio Marín | 24 | Costa Rica |
| 1999 | Australian Open | W | Yevgeny Kafelnikov | 24 | Russia |
| 1999 | Australian Open | F | Thomas Enqvist | 24 | Sweden |
| 1999 | Australian Open | S | Tommy Haas | 20 | Germany |
| 1999 | Australian Open | S | Nicolás Lapentti | 22 | Ecuador |
| 1999 | Australian Open | Q | Vince Spadea | 24 | United States |
| 1999 | Australian Open | Q | Marc Rosset | 28 | Switzerland |
| 1999 | Australian Open | Q | Todd Martin | 28 | United States |
| 1999 | Australian Open | Q | Karol Kučera | 24 | Slovakia |
| 1999 | Australian Open | R16 | Fabrice Santoro | 26 | France |
| 1999 | Australian Open | R16 | Andrei Pavel | 24 | Romania |
| 1999 | Australian Open | R16 | Andre Agassi | 28 | United States |
| 1999 | Australian Open | R16 | Bohdan Ulihrach | 23 | Czech Republic |
| 1999 | Australian Open | R16 | Mark Philippoussis | 22 | Australia |
| 1999 | Australian Open | R16 | Wayne Ferreira | 27 | South Africa |
| 1999 | Australian Open | R16 | Wayne Black | 25 | Zimbabwe |
| 1999 | Australian Open | R16 | Andrew Ilie | 22 | Australia |
| 1999 | Australian Open | R32 | Ján Krošlák | 24 | Slovakia |
| 1999 | Australian Open | R32 | Nicolas Kiefer | 21 | Germany |
| 1999 | Australian Open | R32 | Pat Rafter | 26 | Australia |
| 1999 | Australian Open | R32 | Marat Safin | 18 | Russia |
| 1999 | Australian Open | R32 | Jeff Tarango | 30 | United States |
Open Era Grand Slam Tennis