ATP 250 · 1999-01-11 · draw of 32
Sydney 1999
HardFinal
| 🇺🇸 Todd Martin | d. | 🇪🇸 Alex Corretja | 6-3 7-6(5) | H2H |
Semifinals
| 🇺🇸 Todd Martin | d. | 🇦🇹 Thomas Muster | 6-2 6-1 | H2H |
| 🇪🇸 Alex Corretja | d. | 🇸🇰 Karol Kucera | 7-5 6-4 | H2H |
Quarterfinals
| 🇺🇸 Todd Martin | d. | 🇦🇺 Lleyton Hewitt | 6-3 6-7(4) 6-4 | H2H |
| 🇦🇹 Thomas Muster | d. | 🇦🇺 Jason Stoltenberg | 3-6 6-2 6-3 | H2H |
| 🇸🇰 Karol Kucera | d. | 🇧🇷 Gustavo Kuerten | 3-6 6-4 6-1 | H2H |
| 🇪🇸 Alex Corretja | d. | 🇪🇸 Albert Costa | 6-3 4-6 2-0 RET | H2H |
Round of 16
| 🇦🇺 Lleyton Hewitt | d. | 🇩🇪 Nicolas Kiefer | 6-4 6-2 | H2H |
| 🇺🇸 Todd Martin | d. | 🇦🇷 Mariano Puerta | 7-6(7) 6-4 | H2H |
| 🇦🇹 Thomas Muster | d. | 🇪🇸 Carlos Moya | 7-6(4) 7-5 | H2H |
| 🇦🇺 Jason Stoltenberg | d. | 🇳🇱 Richard Krajicek | 6-3 6-4 | H2H |
| 🇧🇷 Gustavo Kuerten | d. | 🇦🇺 Todd Woodbridge | 6-4 6-0 | H2H |
| 🇸🇰 Karol Kucera | d. | 🇫🇷 Cedric Pioline | 6-4 6-0 | H2H |
| 🇪🇸 Albert Costa | d. | 🇺🇸 Jan-Michael Gambill | 6-3 7-5 | H2H |
| 🇪🇸 Alex Corretja | d. | 🇨🇭 Marc Rosset | 4-6 6-3 7-6(2) | H2H |
Round of 32
| 🇦🇺 Lleyton Hewitt | d. | 🇦🇺 Patrick Rafter | 7-6(1) 6-1 | H2H |
| 🇩🇪 Nicolas Kiefer | d. | 🇨🇿 Martin Damm | 5-7 6-3 6-2 | H2H |
| 🇦🇷 Mariano Puerta | d. | 🇳🇱 Jan Siemerink | 6-2 6-4 | H2H |
| 🇺🇸 Todd Martin | d. | 🇲🇦 Hicham Arazi | 6-1 6-3 | H2H |
| 🇪🇸 Carlos Moya | d. | 🇸🇪 Thomas Johansson | 6-3 7-6(4) | H2H |
| 🇦🇹 Thomas Muster | d. | 🇸🇪 Jonas Bjorkman | 7-5 6-7(2) 6-3 | H2H |
| 🇦🇺 Jason Stoltenberg | d. | 🇪🇸 Alberto Berasategui | 6-1 6-7(3) 7-6(5) | H2H |
| 🇳🇱 Richard Krajicek | d. | 🇫🇷 Jerome Golmard | 6-4 4-0 RET | H2H |
| 🇧🇷 Gustavo Kuerten | d. | 🇬🇧 Greg Rusedski | 1-6 6-3 6-4 | H2H |
| 🇦🇺 Todd Woodbridge | d. | 🇦🇺 Michael Tebbutt | 1-6 6-0 7-6(5) | H2H |
| 🇫🇷 Cedric Pioline | d. | 🇦🇺 Scott Draper | 6-4 7-6(2) | H2H |
| 🇸🇰 Karol Kucera | d. | 🇪🇸 Francisco Clavet | 6-4 7-6(8) | H2H |
| 🇪🇸 Albert Costa | d. | 🇳🇱 Paul Haarhuis | 6-2 6-4 | H2H |
| 🇺🇸 Jan-Michael Gambill | d. | 🇦🇺 Sandon Stolle | 7-6(7) 2-6 6-1 | H2H |
| 🇨🇭 Marc Rosset | d. | 🇨🇿 Bohdan Ulihrach | 6-4 6-0 | H2H |
| 🇪🇸 Alex Corretja | d. | 🇩🇪 Hendrik Dreekmann | 4-6 6-3 6-3 | H2H |