ATP 250 · 1999-01-04 · draw of 32
Adelaide 1999
HardFinal
| 🇸🇪 Thomas Enqvist | d. | 🇦🇺 Lleyton Hewitt | 4-6 6-1 6-2 | H2H |
Semifinals
| 🇸🇪 Thomas Enqvist | d. | 🇦🇺 Scott Draper | 6-3 7-5 | H2H |
| 🇦🇺 Lleyton Hewitt | d. | 🇦🇺 Jason Stoltenberg | 6-1 6-3 | H2H |
Quarterfinals
| 🇸🇪 Thomas Enqvist | d. | 🇸🇰 Dominik Hrbaty | 6-2 6-4 | H2H |
| 🇦🇺 Scott Draper | d. | 🇦🇺 Michael Tebbutt | 6-7(7) 6-4 7-6(5) | H2H |
| 🇦🇺 Jason Stoltenberg | d. | 🇿🇼 Byron Black | 6-3 6-2 | H2H |
| 🇦🇺 Lleyton Hewitt | d. | 🇨🇿 Slava Dosedel | 4-6 6-4 6-2 | H2H |
Round of 16
| 🇸🇪 Thomas Enqvist | d. | 🇩🇪 David Prinosil | 6-2 6-3 | H2H |
| 🇸🇰 Dominik Hrbaty | d. | 🇩🇪 Oliver Gross | W/O | H2H |
| 🇦🇺 Michael Tebbutt | d. | 🇧🇷 Gustavo Kuerten | 6-7(2) 7-6(5) 7-6(3) | H2H |
| 🇦🇺 Scott Draper | d. | 🇺🇸 Michael Chang | 6-3 7-6(6) | H2H |
| 🇿🇼 Byron Black | d. | 🇷🇴 Andrei Pavel | 6-3 6-2 | H2H |
| 🇦🇺 Jason Stoltenberg | d. | 🇮🇹 Gianluca Pozzi | 6-3 6-2 | H2H |
| 🇦🇺 Lleyton Hewitt | d. | 🇨🇿 Jiri Novak | 7-6(2) 2-6 6-4 | H2H |
| 🇨🇿 Slava Dosedel | d. | 🇦🇺 Patrick Rafter | 7-5 6-4 | H2H |
Round of 32
| 🇸🇪 Thomas Enqvist | d. | 🇦🇺 Mark Woodforde | 0-6 6-4 6-4 | H2H |
| 🇩🇪 David Prinosil | d. | 🇷🇴 Adrian Voinea | 7-6(0) 4-6 6-2 | H2H |
| 🇩🇪 Oliver Gross | d. | 🇦🇺 Mark Draper | 6-2 6-0 | H2H |
| 🇸🇰 Dominik Hrbaty | d. | 🇦🇷 Mariano Puerta | 4-6 6-1 7-5 | H2H |
| 🇧🇷 Gustavo Kuerten | d. | 🇫🇷 Jerome Golmard | 7-5 6-1 | H2H |
| 🇦🇺 Michael Tebbutt | d. | 🇨🇦 Sebastien Lareau | 6-3 3-6 6-1 | H2H |
| 🇦🇺 Scott Draper | d. | 🇺🇸 Justin Gimelstob | 3-6 7-6(6) 6-3 | H2H |
| 🇺🇸 Michael Chang | d. | 🇫🇷 Sebastien Grosjean | 6-3 3-6 6-3 | H2H |
| 🇿🇼 Byron Black | d. | 🇺🇸 Vincent Spadea | 1-6 7-6(6) 6-2 | H2H |
| 🇷🇴 Andrei Pavel | d. | 🇸🇪 Mikael Tillstrom | 6-3 6-3 | H2H |
| 🇮🇹 Gianluca Pozzi | d. | 🇦🇺 Todd Woodbridge | 6-4 6-2 | H2H |
| 🇦🇺 Jason Stoltenberg | d. | 🇫🇷 Arnaud Di Pasquale | 6-1 6-4 | H2H |
| 🇦🇺 Lleyton Hewitt | d. | 🇩🇪 Nicolas Kiefer | 7-5 6-4 | H2H |
| 🇨🇿 Jiri Novak | d. | 🇦🇺 Andrew Ilie | 6-2 6-1 | H2H |
| 🇨🇿 Slava Dosedel | d. | 🇺🇸 Jim Courier | 7-5 6-3 | H2H |
| 🇦🇺 Patrick Rafter | d. | 🇯🇵 Takao Suzuki | 6-3 6-0 | H2H |