Chennai 1999 ATP
Final
| Winner | Loser | Score | |
|---|---|---|---|
| Byron Black | d. | Rainer Schuettler | 6-4 1-6 6-3 |
Semifinals
| Winner | Loser | Score | |
|---|---|---|---|
| Rainer Schuettler | d. | Peter Wessels | 6-1 6-3 |
| Byron Black | d. | John Van Lottum | 6-1 6-1 |
Quarterfinals
| Winner | Loser | Score | |
|---|---|---|---|
| Rainer Schuettler | d. | Carlos Moya | 6-1 3-0 RET |
| Peter Wessels | d. | Vincenzo Santopadre | 6-2 6-4 |
| Byron Black | d. | Richard Fromberg | 6-4 6-2 |
| John Van Lottum | d. | Mikael Tillstrom | 4-6 6-3 6-2 |
Round of 16
| Winner | Loser | Score | |
|---|---|---|---|
| Carlos Moya | d. | Wayne Black | 6-3 1-6 7-5 |
| Rainer Schuettler | d. | Andreas Vinciguerra | 6-1 6-2 |
| Peter Wessels | d. | Sargis Sargsian | 7-6(5) 6-7(6) 6-4 |
| Vincenzo Santopadre | d. | Andrew Ilie | 6-2 5-7 6-3 |
| Richard Fromberg | d. | Lars Burgsmuller | 6-4 1-6 6-2 |
| Byron Black | d. | Leander Paes | 6-3 6-2 |
| John Van Lottum | d. | Jonathan Stark | 7-6(12) 0-6 7-6(6) |
| Mikael Tillstrom | d. | Karol Kucera | 7-5 4-6 6-2 |
Round of 32
| Winner | Loser | Score | |
|---|---|---|---|
| Carlos Moya | d. | Vladimir Voltchkov | 4-6 6-3 6-3 |
| Wayne Black | d. | Paul Goldstein | 7-6(6) 6-1 |
| Andreas Vinciguerra | d. | Andre Sa | 6-7(2) 6-2 6-1 |
| Rainer Schuettler | d. | Gaston Etlis | 7-6(5) 6-1 |
| Sargis Sargsian | d. | Thomas Johansson | 6-4 3-0 RET |
| Peter Wessels | d. | Ota Fukarek | 4-6 6-4 7-5 |
| Vincenzo Santopadre | d. | Geoff Grant | 2-6 6-3 6-4 |
| Andrew Ilie | d. | Dennis Van Scheppingen | 6-3 3-6 6-2 |
| Lars Burgsmuller | d. | Sjeng Schalken | 4-6 6-3 6-1 |
| Richard Fromberg | d. | Mahesh Bhupathi | 6-2 7-5 |
| Leander Paes | d. | Andy Zingman | 4-6 6-3 6-4 |
| Byron Black | d. | Gregory Carraz | 6-1 6-3 |
| John Van Lottum | d. | Jens Knippschild | 6-3 6-4 |
| Jonathan Stark | d. | Nicolas Escude | 6-2 6-7(2) 6-2 |
| Mikael Tillstrom | d. | Orlin Stanoytchev | 6-4 6-4 |
| Karol Kucera | d. | Michael Kohlmann | 7-5 6-1 |