ATP 500 · 1999-10-11 · draw of 32
Vienna 1999
HardFinal
| 🇬🇧 Greg Rusedski | d. | 🇩🇪 Nicolas Kiefer | 6-7(5) 2-6 6-3 7-5 6-4 | H2H |
Semifinals
| 🇬🇧 Greg Rusedski | d. | 🇨🇭 Roger Federer | 6-3 6-4 | H2H |
| 🇩🇪 Nicolas Kiefer | d. | 🇳🇱 Richard Krajicek | 7-6(9) 6-4 | H2H |
Quarterfinals
| 🇨🇭 Roger Federer | d. | 🇸🇰 Karol Kucera | 2-6 6-4 6-1 | H2H |
| 🇬🇧 Greg Rusedski | d. | 🇫🇷 Sebastien Grosjean | 7-5 6-2 | H2H |
| 🇳🇱 Richard Krajicek | d. | 🇦🇹 Stefan Koubek | 6-2 6-1 | H2H |
| 🇩🇪 Nicolas Kiefer | d. | 🇷🇺 Yevgeny Kafelnikov | 6-0 6-4 | H2H |
Round of 16
| 🇨🇭 Roger Federer | d. | 🇨🇿 Jiri Novak | 7-6(8) 6-1 | H2H |
| 🇸🇰 Karol Kucera | d. | 🇪🇨 Nicolas Lapentti | 6-2 6-3 | H2H |
| 🇫🇷 Sebastien Grosjean | d. | 🇷🇺 Marat Safin | 6-4 4-6 7-6(5) | H2H |
| 🇬🇧 Greg Rusedski | d. | 🇺🇦 Andrei Medvedev | 4-6 7-5 6-3 | H2H |
| 🇳🇱 Richard Krajicek | d. | 🇸🇪 Magnus Larsson | 6-4 6-2 | H2H |
| 🇦🇹 Stefan Koubek | d. | 🇭🇷 Goran Ivanisevic | 6-7(3) 6-2 6-4 | H2H |
| 🇩🇪 Nicolas Kiefer | d. | 🇦🇹 Jurgen Melzer | 6-4 6-0 | H2H |
| 🇷🇺 Yevgeny Kafelnikov | d. | 🇳🇱 Jan Siemerink | W/O | H2H |
Round of 32
| 🇨🇿 Jiri Novak | d. | 🇺🇸 Todd Martin | 7-6(3) 6-7(5) 6-4 | H2H |
| 🇨🇭 Roger Federer | d. | 🇺🇸 Vincent Spadea | 6-4 6-2 | H2H |
| 🇸🇰 Karol Kucera | d. | 🇸🇰 Dominik Hrbaty | 3-6 6-4 7-6(3) | H2H |
| 🇪🇨 Nicolas Lapentti | d. | 🇪🇸 Francisco Clavet | 7-6(1) 6-2 | H2H |
| 🇷🇺 Marat Safin | d. | 🇬🇧 Tim Henman | 6-4 2-6 6-3 | H2H |
| 🇫🇷 Sebastien Grosjean | d. | 🇨🇭 Marc Rosset | 6-3 4-6 7-6(5) | H2H |
| 🇺🇦 Andrei Medvedev | d. | 🇦🇹 Oliver Marach | 6-4 6-2 | H2H |
| 🇬🇧 Greg Rusedski | d. | 🇸🇪 Thomas Johansson | 4-6 6-3 7-6(3) | H2H |
| 🇳🇱 Richard Krajicek | d. | 🇨🇭 George Bastl | 4-6 7-5 6-4 | H2H |
| 🇸🇪 Magnus Larsson | d. | 🇫🇷 Cedric Pioline | 6-4 7-6(2) | H2H |
| 🇦🇹 Stefan Koubek | d. | 🇺🇸 Jeff Tarango | 6-4 6-4 | H2H |
| 🇭🇷 Goran Ivanisevic | d. | 🇧🇷 Gustavo Kuerten | 6-1 6-7(2) 6-4 | H2H |
| 🇩🇪 Nicolas Kiefer | d. | 🇦🇷 Mariano Zabaleta | 6-3 6-4 | H2H |
| 🇦🇹 Jurgen Melzer | d. | 🇩🇪 Lars Burgsmuller | 7-6(5) 2-6 6-3 | H2H |
| 🇳🇱 Jan Siemerink | d. | 🇫🇷 Arnaud Clement | 5-7 7-6(5) 7-6(6) | H2H |
| 🇷🇺 Yevgeny Kafelnikov | d. | 🇸🇪 Thomas Enqvist | 6-3 6-4 | H2H |