| 1999-11-22 | ATP Tour World Championship | Hard | F | 5 |  Pete Sampras (5) | 1 | Andre Agassi (1) | 6-1 7-5 6-4 | H2H | 3 | 105 | 15 | 10 | 58.8% | 88.0% | 42.9% | 3/4 |
| 1999-11-22 | ATP Tour World Championship | Hard | SF | 1 | Andre Agassi (1) | 2 |  Yevgeny Kafelnikov (2) | 6-4 7-6(5) | 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 | - | - | - | - | - | - | - |
| 1999-11-22 | ATP Tour World Championship | Hard | RR | 1 | Andre Agassi (1) | 5 | Pete Sampras (5) | 6-2 6-2 | 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 | - | - | - | - | - | - | - |
| 1999-11-01 | Paris Masters | Carpet | F | 1 | Andre Agassi (1) | 34 | Marat Safin | 7-6(1) 6-2 4-6 6-4 | H2H | 5 | 149 | 7 | 2 | 61.9% | 69.9% | 56.9% | 10/13 |
| 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 | 1 | Andre Agassi (1) | 22 |  Mark Philippoussis | 6-4 6-1 | H2H | 3 | 64 | 9 | 1 | 62.8% | 100.0% | 56.3% | 0/0 |
| 1999-11-01 | Paris Masters | Carpet | R16 | 1 | Andre Agassi (1) | 49 |  Sjeng Schalken (Q) | 6-4 3-6 6-2 | H2H | 3 | 96 | 7 | 6 | 55.6% | 94.3% | 50.0% | 3/5 |
| 1999-11-01 | Paris Masters | Carpet | R32 | 1 | Andre Agassi (1) | 29 | MARYounes El Aynaoui | 6-4 6-3 | H2H | 3 | 57 | 7 | 0 | 50.0% | 90.0% | 90.0% | 0/0 |
