| 1999-04-26 | Prague | Clay | R32 | 78 |  Slava Dosedel | 145 |  David Nainkin | 7-6(5) 6-4 | H2H | 3 | 84 | 2 | 3 | 71.0% | 59.2% | 45.0% | 4/9 |
| 1999-04-02 | Davis Cup G1 QF: RSA vs BLR | Hard | RR | 129 |  Vladimir Voltchkov | 139 | David Nainkin | 3-6 7-5 6-4 7-6(5) | H2H | 5 | - | - | - | - | - | - | - |
| 1999-04-02 | Davis Cup G1 QF: RSA vs BLR | Hard | RR | 139 | David Nainkin | 1038 | Sergei Samoseiko | 6-2 6-2 | H2H | 3 | - | - | - | - | - | - | - |
| 1998-10-26 | Stuttgart Masters | Hard | R64 | 37 |  Tommy Haas | 155 | David Nainkin (LL) | 6-4 6-4 | H2H | 3 | 68 | 7 | 1 | 59.6% | 87.1% | 66.7% | 0/0 |
| 1998-09-25 | Davis Cup WG PO: CZE vs RSA | Clay | RR | 32 | Bohdan Ulihrach | 148 | David Nainkin | 6-0 6-1 | H2H | 3 | - | - | - | - | - | - | - |
| 1998-09-14 | Tashkent | Hard | R16 | 11 |  Yevgeny Kafelnikov (1) | 188 | David Nainkin | 6-3 6-0 | H2H | 3 | 53 | 5 | 4 | 40.0% | 93.8% | 75.0% | 2/2 |
| 1998-09-14 | Tashkent | Hard | R32 | 188 | David Nainkin | 120 |  Lionel Roux | 3-6 6-2 6-3 | H2H | 3 | 97 | 6 | 6 | 54.9% | 64.4% | 67.6% | 6/8 |
| 1998-08-31 | US Open | Hard | R32 | 3 |  Patrick Rafter (3) | 188 | David Nainkin (Q) | 6-1 6-1 6-1 | H2H | 5 | - | 5 | 0 | 74.6% | 86.4% | 73.3% | 0/0 |
| 1998-08-31 | US Open | Hard | R64 | 188 | David Nainkin (Q) | 25 |  Gustavo Kuerten | 2-6 6-4 6-3 6-4 | H2H | 5 | - | 4 | 8 | 65.7% | 65.6% | 42.6% | 8/13 |
| 1998-08-31 | US Open | Hard | R128 | 188 | David Nainkin (Q) | 358 |  Mark Merklein (Q) | 6-7(3) 6-0 6-4 6-4 | H2H | 5 | - | 9 | 7 | 57.2% | 79.5% | 50.0% | 9/10 |
