| 2000-07-14 | Davis Cup WG PO: UZB vs NED | Clay | RR | 586 |  Paul Haarhuis | 172 |  Vadim Kutsenko | 6-1 6-2 | H2H | 3 | - | - | - | - | - | - | - |
| 1999-08-30 | US Open | Hard | R64 | 6 |  Gustavo Kuerten (5) | 122 | Paul Haarhuis | 6-3 7-6(4) 3-6 6-2 | H2H | 5 | 131 | 16 | 1 | 49.2% | 82.0% | 54.0% | 5/8 |
| 1999-08-30 | US Open | Hard | R128 | 122 | Paul Haarhuis | 99 |  Hendrik Dreekmann | 6-4 6-1 6-4 | H2H | 5 | 111 | 5 | 3 | 53.5% | 77.4% | 54.3% | 7/8 |
| 1999-08-23 | Boston | Hard | R32 | 51 | Sjeng Schalken | 88 | Paul Haarhuis | 4-6 6-3 6-0 | H2H | 3 | 98 | 4 | 8 | 55.9% | 63.2% | 60.0% | 12/14 |
| 1999-08-16 | Indianapolis | Hard | R64 | 54 | David Prinosil | 88 | Paul Haarhuis | 6-3 6-2 | H2H | 3 | 66 | 3 | 3 | 54.9% | 67.9% | 69.6% | 4/5 |
| 1999-08-02 | Amsterdam | Clay | R32 | 35 |  Andrei Medvedev (7) | 92 | Paul Haarhuis (WC) | 7-5 6-3 | H2H | 3 | 90 | 4 | 5 | 56.9% | 75.8% | 72.0% | 1/1 |
| 1999-06-21 | Wimbledon | Grass | R32 | 15 |  Goran Ivanisevic (10) | 93 | Paul Haarhuis | 7-6(2) 6-4 7-6(3) | H2H | 5 | 126 | 21 | 12 | 52.4% | 88.3% | 50.0% | 7/8 |
| 1999-06-21 | Wimbledon | Grass | R64 | 93 | Paul Haarhuis | 46 |  Fernando Vicente | 6-2 6-2 6-2 | H2H | 5 | 68 | 4 | 0 | 73.0% | 81.5% | 60.0% | 3/3 |
| 1999-06-21 | Wimbledon | Grass | R128 | 93 | Paul Haarhuis | 37 | MARHicham Arazi | 7-6(4) 6-3 6-2 | H2H | 5 | 101 | 4 | 1 | 66.3% | 81.0% | 59.4% | 0/0 |
| 1999-06-14 | 's-Hertogenbosch | Grass | R32 | 2 |  Patrick Rafter (2) | 92 | Paul Haarhuis | 4-6 7-6(5) 6-3 | H2H | 3 | 113 | 12 | 2 | 65.2% | 86.7% | 50.0% | 3/4 |
