Masters · 1999-10-25 · draw of 48
Stuttgart Masters 1999
HardFinal
| 🇸🇪 Thomas Enqvist | d. | 🇳🇱 Richard Krajicek | 6-1 6-4 5-7 7-5 | H2H |
Semifinals
| 🇳🇱 Richard Krajicek | d. | 🇬🇧 Greg Rusedski | 6-4 6-4 | H2H |
| 🇸🇪 Thomas Enqvist | d. | 🇺🇸 Andre Agassi | 6-3 4-6 6-0 | H2H |
Quarterfinals
| 🇳🇱 Richard Krajicek | d. | 🇦🇷 Mariano Zabaleta | 6-3 6-2 | H2H |
| 🇬🇧 Greg Rusedski | d. | 🇺🇸 Todd Martin | 4-6 7-6(10) 6-4 | H2H |
| 🇸🇪 Thomas Enqvist | d. | 🇨🇱 Marcelo Rios | 6-4 6-2 | H2H |
| 🇺🇸 Andre Agassi | d. | 🇷🇴 Andrei Pavel | 6-2 6-1 | H2H |
Round of 16
| 🇦🇷 Mariano Zabaleta | d. | 🇸🇪 Magnus Norman | 6-3 6-4 | H2H |
| 🇳🇱 Richard Krajicek | d. | 🇪🇸 Alex Corretja | 7-6(4) 7-6(5) | H2H |
| 🇺🇸 Todd Martin | d. | 🇨🇿 Jiri Novak | 6-2 6-4 | H2H |
| 🇬🇧 Greg Rusedski | d. | 🇩🇪 Tommy Haas | 6-4 6-3 | H2H |
| 🇨🇱 Marcelo Rios | d. | 🇪🇨 Nicolas Lapentti | 6-4 6-3 | H2H |
| 🇸🇪 Thomas Enqvist | d. | 🇧🇷 Gustavo Kuerten | 6-4 5-7 6-4 | H2H |
| 🇷🇴 Andrei Pavel | d. | 🇨🇿 Daniel Vacek | 6-4 7-5 | H2H |
| 🇺🇸 Andre Agassi | d. | 🇳🇱 Sjeng Schalken | 6-4 6-2 | H2H |
Round of 32
| 🇦🇷 Mariano Zabaleta | d. | 🇷🇺 Yevgeny Kafelnikov | 6-3 6-3 | H2H |
| 🇸🇪 Magnus Norman | d. | 🇷🇺 Marat Safin | 6-4 7-5 | H2H |
| 🇪🇸 Alex Corretja | d. | 🇺🇸 Jim Courier | 6-3 6-7(5) 6-3 | H2H |
| 🇳🇱 Richard Krajicek | d. | 🇺🇸 Chris Woodruff | 6-4 7-6(3) | H2H |
| 🇺🇸 Todd Martin | d. | 🇫🇷 Fabrice Santoro | 6-4 6-2 | H2H |
| 🇨🇿 Jiri Novak | d. | 🇫🇷 Cedric Pioline | 6-4 3-6 6-3 | H2H |
| 🇩🇪 Tommy Haas | d. | 🇿🇦 Wayne Ferreira | 6-2 7-6(2) | H2H |
| 🇬🇧 Greg Rusedski | d. | 🇸🇪 Magnus Larsson | W/O | H2H |
| 🇨🇱 Marcelo Rios | d. | 🇫🇷 Sebastien Grosjean | 6-3 6-4 | H2H |
| 🇪🇨 Nicolas Lapentti | d. | 🇸🇰 Dominik Hrbaty | 3-6 6-4 6-3 | H2H |
| 🇸🇪 Thomas Enqvist | d. | 🇺🇸 Michael Chang | 6-4 6-2 | H2H |
| 🇧🇷 Gustavo Kuerten | d. | 🇪🇸 Albert Costa | 3-6 7-5 6-3 | H2H |
| 🇷🇴 Andrei Pavel | d. | 🇩🇪 Nicolas Kiefer | 6-5 RET | H2H |
| 🇨🇿 Daniel Vacek | d. | 🇬🇧 Tim Henman | 6-3 6-1 | H2H |
| 🇳🇱 Sjeng Schalken | d. | 🇸🇰 Karol Kucera | 7-5 6-1 | H2H |
| 🇺🇸 Andre Agassi | d. | 🇦🇺 Mark Philippoussis | 6-2 6-4 | H2H |
Round of 64
| 🇦🇷 Mariano Zabaleta | d. | 🇺🇸 Vincent Spadea | 6-4 3-6 6-1 | H2H |
| 🇷🇺 Marat Safin | d. | 🇦🇺 Lleyton Hewitt | 7-6(7) 3-6 6-2 | H2H |
| 🇺🇸 Jim Courier | d. | 🇨🇭 Marc Rosset | 4-6 7-6(6) 6-2 | H2H |
| 🇺🇸 Chris Woodruff | d. | 🇪🇸 Francisco Clavet | 6-1 6-4 | H2H |
| 🇫🇷 Fabrice Santoro | d. | 🇲🇦 Younes El Aynaoui | 6-2 6-4 | H2H |
| 🇨🇿 Jiri Novak | d. | 🇭🇷 Goran Ivanisevic | 6-2 3-6 7-6(2) | H2H |
| 🇿🇦 Wayne Ferreira | d. | 🇺🇸 Justin Gimelstob | 6-4 4-6 6-4 | H2H |
| 🇸🇪 Magnus Larsson | d. | 🇮🇹 Laurence Tieleman | 7-6(4) 6-7(6) 6-2 | H2H |
| 🇫🇷 Sebastien Grosjean | d. | 🇪🇸 Fernando Vicente | 6-2 6-2 | H2H |
| 🇸🇰 Dominik Hrbaty | d. | 🇸🇪 Thomas Johansson | 6-7(3) 7-6(4) 6-1 | H2H |
| 🇺🇸 Michael Chang | d. | 🇩🇪 Rainer Schuettler | 3-6 7-6(4) 6-2 | H2H |
| 🇪🇸 Albert Costa | d. | 🇲🇦 Hicham Arazi | 7-5 2-6 6-3 | H2H |
| 🇷🇴 Andrei Pavel | d. | 🇧🇷 Fernando Meligeni | 3-6 6-3 6-4 | H2H |
| 🇨🇿 Daniel Vacek | d. | 🇺🇦 Andrei Medvedev | 6-1 2-1 RET | H2H |
| 🇳🇱 Sjeng Schalken | d. | 🇫🇷 Arnaud Clement | 7-5 7-6(4) | H2H |
| 🇦🇺 Mark Philippoussis | d. | 🇮🇹 Gianluca Pozzi | 6-4 4-6 7-5 | H2H |