ATP 500 · 1999-10-11 · draw of 32
Singapore 1999
HardFinal
| 🇨🇱 Marcelo Rios | d. | 🇸🇪 Mikael Tillstrom | 6-2 7-6(5) | H2H |
Semifinals
| 🇸🇪 Mikael Tillstrom | d. | 🇹🇭 Paradorn Srichaphan | 6-4 3-6 6-3 | H2H |
| 🇨🇱 Marcelo Rios | d. | 🇦🇺 Lleyton Hewitt | 7-5 6-3 | H2H |
Quarterfinals
| 🇸🇪 Mikael Tillstrom | d. | 🇭🇷 Ivan Ljubicic | 7-6(4) 4-6 6-3 | H2H |
| 🇹🇭 Paradorn Srichaphan | d. | 🇦🇺 Andrew Ilie | 7-5 3-6 7-6(3) | H2H |
| 🇦🇺 Lleyton Hewitt | d. | 🇳🇱 John van Lottum | 6-4 6-2 | H2H |
| 🇨🇱 Marcelo Rios | d. | 🇺🇸 Jan-Michael Gambill | 6-4 6-4 | H2H |
Round of 16
| 🇭🇷 Ivan Ljubicic | d. | 🇦🇺 Mark Philippoussis | 3-6 7-5 7-6(6) | H2H |
| 🇸🇪 Mikael Tillstrom | d. | 🇸🇪 Jonas Bjorkman | 3-6 6-4 6-3 | H2H |
| 🇹🇭 Paradorn Srichaphan | d. | 🇫🇷 Antony Dupuis | 6-4 6-1 | H2H |
| 🇦🇺 Andrew Ilie | d. | 🇫🇷 Stephane Huet | 7-6(6) 5-7 6-3 | H2H |
| 🇳🇱 John van Lottum | d. | 🇦🇺 Todd Woodbridge | 6-4 6-0 | H2H |
| 🇦🇺 Lleyton Hewitt | d. | 🇩🇰 Kenneth Carlsen | 6-1 6-2 | H2H |
| 🇺🇸 Jan-Michael Gambill | d. | 🇺🇸 Michael Chang | 6-2 7-6(4) | H2H |
| 🇨🇱 Marcelo Rios | d. | 🇨🇦 Daniel Nestor | 6-4 6-1 | H2H |
Round of 32
| 🇦🇺 Mark Philippoussis | d. | 🇺🇸 Bob Bryan | 6-4 6-4 | H2H |
| 🇭🇷 Ivan Ljubicic | d. | 🇧🇾 Max Mirnyi | 7-6(1) 6-4 | H2H |
| 🇸🇪 Mikael Tillstrom | d. | 🇿🇼 Byron Black | 6-3 6-4 | H2H |
| 🇸🇪 Jonas Bjorkman | d. | 🇦🇺 Richard Fromberg | 7-5 6-2 | H2H |
| 🇹🇭 Paradorn Srichaphan | d. | 🇸🇪 Magnus Norman | 6-3 1-6 6-3 | H2H |
| 🇫🇷 Antony Dupuis | d. | 🇦🇺 Mark Woodforde | 3-6 6-4 7-6(2) | H2H |
| 🇫🇷 Stephane Huet | d. | 🇸🇪 Nicklas Kulti | 7-5 6-4 | H2H |
| 🇦🇺 Andrew Ilie | d. | 🇵🇾 Ramon Delgado | 6-2 6-2 | H2H |
| 🇦🇺 Todd Woodbridge | d. | 🇳🇱 Sjeng Schalken | 4-6 7-5 6-3 | H2H |
| 🇳🇱 John van Lottum | d. | 🇦🇺 Wayne Arthurs | 7-6(2) 7-6(7) | H2H |
| 🇩🇰 Kenneth Carlsen | d. | 🇨🇦 Sebastien Lareau | 6-4 3-6 6-2 | H2H |
| 🇦🇺 Lleyton Hewitt | d. | 🇺🇸 Paul Goldstein | 4-6 6-2 6-4 | H2H |
| 🇺🇸 Jan-Michael Gambill | d. | 🇺🇸 Justin Gimelstob | 7-6(2) 6-4 | H2H |
| 🇺🇸 Michael Chang | d. | 🇮🇳 Leander Paes | 6-1 6-3 | H2H |
| 🇨🇦 Daniel Nestor | d. | 🇵🇭 Cecil Mamiit | 6-3 4-6 6-4 | H2H |
| 🇨🇱 Marcelo Rios | d. | 🇸🇪 Fredrik Jonsson | 6-4 6-2 | H2H |