ATP 250 · 1999-04-05 · draw of 32
Chennai 1999
HardFinal
| 🇿🇼 Byron Black | d. | 🇩🇪 Rainer Schuettler | 6-4 1-6 6-3 | H2H |
Semifinals
| 🇿🇼 Byron Black | d. | 🇳🇱 John van Lottum | 6-1 6-1 | H2H |
| 🇩🇪 Rainer Schuettler | d. | 🇳🇱 Peter Wessels | 6-1 6-3 | H2H |
Quarterfinals
| 🇳🇱 John van Lottum | d. | 🇸🇪 Mikael Tillstrom | 4-6 6-3 6-2 | H2H |
| 🇿🇼 Byron Black | d. | 🇦🇺 Richard Fromberg | 6-4 6-2 | H2H |
| 🇳🇱 Peter Wessels | d. | 🇮🇹 Vincenzo Santopadre | 6-2 6-4 | H2H |
| 🇩🇪 Rainer Schuettler | d. | 🇪🇸 Carlos Moya | 6-1 3-0 RET | H2H |
Round of 16
| 🇸🇪 Mikael Tillstrom | d. | 🇸🇰 Karol Kucera | 7-5 4-6 6-2 | H2H |
| 🇳🇱 John van Lottum | d. | 🇺🇸 Jonathan Stark | 7-6(12) 0-6 7-6(6) | H2H |
| 🇿🇼 Byron Black | d. | 🇮🇳 Leander Paes | 6-3 6-2 | H2H |
| 🇦🇺 Richard Fromberg | d. | 🇩🇪 Lars Burgsmuller | 6-4 1-6 6-2 | H2H |
| 🇮🇹 Vincenzo Santopadre | d. | 🇦🇺 Andrew Ilie | 6-2 5-7 6-3 | H2H |
| 🇳🇱 Peter Wessels | d. | 🇦🇲 Sargis Sargsian | 7-6(5) 6-7(6) 6-4 | H2H |
| 🇩🇪 Rainer Schuettler | d. | 🇸🇪 Andreas Vinciguerra | 6-1 6-2 | H2H |
| 🇪🇸 Carlos Moya | d. | 🇿🇼 Wayne Black | 6-3 1-6 7-5 | H2H |
Round of 32
| 🇸🇰 Karol Kucera | d. | 🇩🇪 Michael Kohlmann | 7-5 6-1 | H2H |
| 🇸🇪 Mikael Tillstrom | d. | 🇧🇬 Orlin Stanoytchev | 6-4 6-4 | H2H |
| 🇺🇸 Jonathan Stark | d. | 🇫🇷 Nicolas Escude | 6-2 6-7(2) 6-2 | H2H |
| 🇳🇱 John van Lottum | d. | 🇩🇪 Jens Knippschild | 6-3 6-4 | H2H |
| 🇿🇼 Byron Black | d. | 🇫🇷 Gregory Carraz | 6-1 6-3 | H2H |
| 🇮🇳 Leander Paes | d. | 🇦🇷 Andy Zingman | 4-6 6-3 6-4 | H2H |
| 🇦🇺 Richard Fromberg | d. | 🇮🇳 Mahesh Bhupathi | 6-2 7-5 | H2H |
| 🇩🇪 Lars Burgsmuller | d. | 🇳🇱 Sjeng Schalken | 4-6 6-3 6-1 | H2H |
| 🇦🇺 Andrew Ilie | d. | 🇳🇱 Dennis Van Scheppingen | 6-3 3-6 6-2 | H2H |
| 🇮🇹 Vincenzo Santopadre | d. | 🇺🇸 Geoff Grant | 2-6 6-3 6-4 | H2H |
| 🇳🇱 Peter Wessels | d. | 🇨🇿 Ota Fukarek | 4-6 6-4 7-5 | H2H |
| 🇦🇲 Sargis Sargsian | d. | 🇸🇪 Thomas Johansson | 6-4 3-0 RET | H2H |
| 🇩🇪 Rainer Schuettler | d. | 🇦🇷 Gaston Etlis | 7-6(5) 6-1 | H2H |
| 🇸🇪 Andreas Vinciguerra | d. | 🇧🇷 Andre Sa | 6-7(2) 6-2 6-1 | H2H |
| 🇿🇼 Wayne Black | d. | 🇺🇸 Paul Goldstein | 7-6(6) 6-1 | H2H |
| 🇪🇸 Carlos Moya | d. | 🇧🇾 Vladimir Voltchkov | 4-6 6-3 6-3 | H2H |