| 1999-11-22 | ATP Tour World Championship | Hard | RR | 5 |  Pete Sampras (5) | 3 |  Gustavo Kuerten (3) | 6-2 6-3 | H2H | 3 | - | - | - | - | - | - | - |
| 1999-11-22 | ATP Tour World Championship | Hard | RR | 1 | Andre Agassi (1) | 3 | Gustavo Kuerten (3) | 6-4 7-5 | H2H | 3 | - | - | - | - | - | - | - |
| 1999-11-22 | ATP Tour World Championship | Hard | RR | 3 | Gustavo Kuerten (3) | 8 |  Nicolas Lapentti (8) | 6-1 6-2 | H2H | 3 | - | - | - | - | - | - | - |
| 1999-11-01 | Paris Masters | Carpet | R32 | 34 |  Marat Safin | 5 | Gustavo Kuerten (5) | 7-6(4) 3-6 7-6(4) | H2H | 3 | 116 | 15 | 2 | 44.8% | 76.6% | 51.7% | 5/11 |
| 1999-10-25 | Stuttgart Masters | Hard | R16 | 18 |  Thomas Enqvist (13) | 5 | Gustavo Kuerten (4) | 6-4 5-7 6-4 | H2H | 3 | 99 | 12 | 3 | 48.9% | 81.8% | 43.5% | 3/7 |
| 1999-10-25 | Stuttgart Masters | Hard | R32 | 5 | Gustavo Kuerten (4) | 24 |  Albert Costa | 3-6 7-5 6-3 | H2H | 3 | 113 | 14 | 5 | 43.3% | 83.3% | 41.8% | 8/12 |
| 1999-10-18 | Lyon | Carpet | QF | 14 | Nicolas Lapentti (6) | 5 | Gustavo Kuerten (3) | 5-7 6-4 7-5 | H2H | 3 | 159 | 5 | 3 | 56.8% | 74.6% | 43.8% | 4/8 |
| 1999-10-18 | Lyon | Carpet | R16 | 5 | Gustavo Kuerten (3) | 41 |  Wayne Ferreira | 7-6(5) 6-3 | H2H | 3 | 80 | 3 | 1 | 46.2% | 93.3% | 51.4% | 4/6 |
| 1999-10-18 | Lyon | Carpet | R32 | 5 | Gustavo Kuerten (3) | 49 | Fernando Vicente | 6-3 7-6(4) | H2H | 3 | 70 | 15 | 5 | 49.3% | 86.5% | 42.1% | 3/5 |
| 1999-10-11 | Vienna | Hard | R32 | 43 |  Goran Ivanisevic | 5 | Gustavo Kuerten (3) | 6-1 6-7(2) 6-4 | H2H | 3 | 96 | 18 | 5 | 59.8% | 93.9% | 51.5% | 0/0 |
