| 1999-11-22 | ATP Tour World Championship | Hard | RR | 5 |  Pete Sampras (5) | 8 |  Nicolas Lapentti (8) | 7-6(2) 7-6(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 | - | - | - | - | - | - | - |
| 1999-11-22 | ATP Tour World Championship | Hard | RR | 1 | Andre Agassi (1) | 8 | Nicolas Lapentti (8) | 6-1 6-2 | H2H | 3 | - | - | - | - | - | - | - |
| 1999-11-08 | Stockholm | Hard | QF | 19 |  Magnus Norman (6) | 8 | Nicolas Lapentti (3) | 6-1 6-4 | H2H | 3 | 66 | 6 | 3 | 57.8% | 84.6% | 63.2% | 1/2 |
| 1999-11-08 | Stockholm | Hard | R16 | 8 | Nicolas Lapentti (3) | 429 |  Filip Dewulf (Q) | 5-7 6-3 6-3 | H2H | 3 | 110 | 9 | 5 | 51.0% | 78.4% | 40.8% | 5/8 |
| 1999-11-08 | Stockholm | Hard | R32 | 8 | Nicolas Lapentti (3) | 91 |  Peter Wessels | 6-4 7-6(5) | H2H | 3 | 92 | 6 | 0 | 58.4% | 71.1% | 59.4% | 4/6 |
| 1999-11-01 | Paris Masters | Carpet | SF | 1 | Andre Agassi (1) | 11 | Nicolas Lapentti (11) | 3-6 6-3 6-2 | H2H | 3 | 112 | 3 | 2 | 64.7% | 72.7% | 58.3% | 1/4 |
| 1999-11-01 | Paris Masters | Carpet | QF | 11 | Nicolas Lapentti (11) | 14 |  Tommy Haas (13) | 6-4 3-6 6-3 | H2H | 3 | 95 | 5 | 4 | 60.5% | 82.6% | 60.0% | 5/6 |
| 1999-11-01 | Paris Masters | Carpet | R16 | 11 | Nicolas Lapentti (11) | 24 |  Albert Costa | 6-2 7-5 | H2H | 3 | 83 | 5 | 2 | 58.7% | 67.6% | 69.2% | 1/2 |
| 1999-11-01 | Paris Masters | Carpet | R32 | 11 | Nicolas Lapentti (11) | 38 |  Fabrice Santoro | 6-3 7-6(5) | H2H | 3 | 87 | 4 | 0 | 60.0% | 75.0% | 62.5% | 5/7 |
