| 1999-06-21 | Wimbledon | Grass | R128 | 7 |  Gustavo Kuerten (11) | 198 |  Chris Wilkinson (WC) | 6-4 6-4 6-4 | H2H | 5 | 85 | 16 | 3 | 58.7% | 93.8% | 46.7% | 4/4 |
| 1999-06-14 | Nottingham | Grass | R32 | 62 |  Andrew Ilie | 200 | Chris Wilkinson (WC) | 7-6(4) 6-7(5) 6-4 | H2H | 3 | 153 | 12 | 4 | 57.5% | 73.8% | 54.2% | 8/11 |
| 1999-06-07 | Queen's Club | Grass | R32 | 42 | Lleyton Hewitt (14) | 202 | Chris Wilkinson (WC) | 6-4 6-3 | H2H | 3 | 77 | 5 | 0 | 61.8% | 76.5% | 42.9% | 2/4 |
| 1999-06-07 | Queen's Club | Grass | R64 | 202 | Chris Wilkinson (WC) | 106 |  Takao Suzuki | 4-6 7-6(5) 6-1 | H2H | 3 | 118 | 3 | 3 | 76.6% | 65.3% | 59.1% | 5/7 |
| 1998-09-25 | Davis Cup WG PO: GBR vs IND | Hard | RR | 363 |  Mahesh Bhupathi | 144 | Chris Wilkinson | 6-3 6-4 | H2H | 3 | - | - | - | - | - | - | - |
| 1998-09-14 | Bournemouth | Clay | R32 | 137 |  Jan Kroslak | 135 | Chris Wilkinson | 6-4 7-5 | H2H | 3 | 92 | 6 | 6 | 63.9% | 66.0% | 56.7% | 6/7 |
| 1998-06-22 | Wimbledon | Grass | R32 | 27 |  Wayne Ferreira | 156 | Chris Wilkinson (WC) | 6-2 4-6 6-3 6-1 | H2H | 5 | 145 | 14 | 13 | 45.6% | 75.0% | 40.7% | 14/18 |
| 1998-06-22 | Wimbledon | Grass | R64 | 156 | Chris Wilkinson (WC) | 39 |  Marc Rosset | 6-4 6-4 7-6(3) | H2H | 5 | 117 | 3 | 4 | 65.1% | 69.6% | 43.2% | 3/7 |
| 1998-06-22 | Wimbledon | Grass | R128 | 156 | Chris Wilkinson (WC) | 1122 |  Mark Knowles (Q) | 7-5 6-0 6-1 | H2H | 5 | 102 | 3 | 2 | 66.3% | 74.6% | 40.0% | 6/8 |
| 1998-06-15 | Nottingham | Grass | R32 | 90 |  Jordi Burillo | 157 | Chris Wilkinson (WC) | 6-2 6-2 | H2H | 3 | 59 | 7 | 0 | 50.0% | 100.0% | 68.4% | 0/0 |
