| 2000-01-17 | Australian Open | Hard | R64 | 43 |  Stefan Koubek | 472 |  Grant Stafford (Q) | 5-7 7-5 2-6 6-2 6-3 | H2H | 5 | 158 | 7 | 4 | 62.7% | 66.3% | 50.0% | 13/20 |
| 2000-01-17 | Australian Open | Hard | R128 | 472 | Grant Stafford (Q) | 23 |  Marat Safin | 7-6(4) 6-4 6-1 | H2H | 5 | 96 | 11 | 3 | 72.1% | 87.1% | 50.0% | 4/5 |
| 1999-09-24 | Davis Cup WG PO: GBR vs RSA | Hard | RR | 7 |  Tim Henman | 500 | Grant Stafford | 6-3 7-5 7-6(6) | H2H | 5 | - | - | - | - | - | - | - |
| 1999-09-24 | Davis Cup WG PO: GBR vs RSA | Hard | RR | 6 | Greg Rusedski | 500 | Grant Stafford | 6-4 7-5 | H2H | 3 | - | - | - | - | - | - | - |
| 1999-08-16 | Indianapolis | Hard | R64 | 20 |  Nicolas Lapentti (11) | 520 | Grant Stafford (Q) | 6-3 7-5 | H2H | 3 | 77 | 8 | 4 | 58.4% | 73.3% | 56.3% | 5/6 |
| 1999-06-21 | Wimbledon | Grass | R128 | 36 |  Jonas Bjorkman | 434 | Grant Stafford (Q) | 6-4 6-1 6-4 | H2H | 5 | 102 | 7 | 6 | 55.8% | 75.9% | 45.7% | 9/10 |
| 1999-02-15 | Memphis | Hard | R64 | 185 |  Alex O'Brien (WC) | 172 | Grant Stafford (Q) | 6-4 6-2 | H2H | 3 | 85 | 11 | 1 | 69.6% | 68.8% | 52.4% | 3/4 |
| 1998-08-17 | Indianapolis | Hard | R64 | 22 |  Mark Philippoussis (11) | 125 | Grant Stafford | 6-3 6-2 | H2H | 3 | 61 | 8 | 5 | 51.7% | 76.7% | 53.6% | 2/3 |
| 1998-08-03 | Canada Masters | Hard | R64 | 91 |  Guillermo Canas | 113 | Grant Stafford | 2-6 7-6(13) 6-2 | H2H | 3 | 116 | 8 | 5 | 52.6% | 66.0% | 51.1% | 4/8 |
| 1998-07-27 | Los Angeles | Hard | R32 | 12 | Tim Henman (2) | 115 | Grant Stafford | 6-3 6-0 | H2H | 3 | 57 | 10 | 2 | 57.1% | 87.5% | 66.7% | 1/1 |
