| Year | Tournament | Result | Player | Age | Nation |
|---|---|---|---|---|---|
| 1999 | Australian Open | W | Yevgeny Kafelnikov | 24 | Russia |
| 1999 | Australian Open | W | Martina Hingis | 18 | Switzerland |
| 1999 | Australian Open | F | Thomas Enqvist | 24 | Sweden |
| 1999 | Australian Open | F | Amélie Mauresmo | 19 | France |
| 1999 | Australian Open | S | Tommy Haas | 20 | Germany |
| 1999 | Australian Open | S | Nicolás Lapentti | 22 | Ecuador |
| 1999 | Australian Open | S | Monica Seles | 25 | United States |
| 1999 | Australian Open | S | Lindsay Davenport | 22 | United States |
| 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 | Q | Mary Pierce | 24 | France |
| 1999 | Australian Open | Q | Dominique Monami | 25 | Belgium |
| 1999 | Australian Open | Q | Steffi Graf | 29 | Germany |
| 1999 | Australian Open | Q | Venus Williams | 18 | United States |
| 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 | R16 | Chanda Rubin | 22 | United States |
| 1999 | Australian Open | R16 | Maureen Drake | 27 | Canada |
| 1999 | Australian Open | R16 | Anna Kournikova | 17 | Russia |
| 1999 | Australian Open | R16 | Émilie Loit | 19 | France |
| 1999 | Australian Open | R16 | Sandrine Testud | 26 | France |
| 1999 | Australian Open | R16 | Barbara Schett | 22 | Austria |
| 1999 | Australian Open | R16 | María Sánchez Lorenzo | 21 | Spain |
| 1999 | Australian Open | R16 | Amanda Coetzer | 27 | South Africa |
| 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 |
| 1999 | Australian Open | R32 | Richard Krajicek | 27 | Netherlands |
| 1999 | Australian Open | R32 | Mikael Tillström | 26 | Sweden |
| 1999 | Australian Open | R32 | Jiří Novák | 23 | Czech Republic |
| 1999 | Australian Open | R32 | Martin Damm (born 1972) | 26 | Czech Republic |
| 1999 | Australian Open | R32 | Daniel Nestor | 26 | Canada |
| 1999 | Australian Open | R32 | Christian Ruud | 26 | Norway |
| 1999 | Australian Open | R32 | Gianluca Pozzi | 33 | Italy |
| 1999 | Australian Open | R32 | Tim Henman | 24 | United Kingdom |
| 1999 | Australian Open | R32 | Jim Courier | 28 | United States |
| 1999 | Australian Open | R32 | Paul Goldstein | 22 | United States |
| 1999 | Australian Open | R32 | Petr Korda | 31 | Czech Republic |
| 1999 | Australian Open | R32 | Karina Habšudová | 25 | Slovakia |
| 1999 | Australian Open | R32 | Janet Lee | 22 | Taiwan |
Open Era Grand Slam Tennis