| 2001-06-25 | Wimbledon | Grass | R128 | 4 |  Juan Carlos Ferrero (8) | 522 |  Luke Milligan (Q) | 6-0 6-2 6-2 | H2H | 5 | 84 | 4 | 1 | 72.3% | 74.5% | 50.0% | 2/3 |
| 2000-11-20 | Brighton | Hard | R32 | 52 |  Vladimir Voltchkov (5) | 544 | Luke Milligan (WC) | 6-7(1) 6-3 6-1 | H2H | 3 | 106 | 5 | 9 | 57.3% | 76.4% | 46.3% | 6/8 |
| 1999-06-21 | Wimbledon | Grass | R128 | 43 |  Fabrice Santoro | 272 | Luke Milligan (WC) | 6-4 7-5 7-6(0) | H2H | 5 | 109 | 4 | 2 | 59.0% | 80.6% | 60.5% | 0/1 |
| 1999-06-14 | Nottingham | Grass | R16 | 45 | Fabrice Santoro | 314 | Luke Milligan (WC) | 6-4 6-2 | H2H | 3 | 71 | 3 | 0 | 63.0% | 86.2% | 64.7% | 0/0 |
| 1999-06-14 | Nottingham | Grass | R32 | 314 | Luke Milligan (WC) | 41 |  Byron Black (6) | 6-4 3-6 6-2 | H2H | 3 | 112 | 9 | 4 | 52.9% | 69.6% | 41.5% | 3/7 |
| 1997-06-23 | Wimbledon | Grass | R128 | 228 | Arnaud Clement (Q) | 295 | Luke Milligan (WC) | 2-6 7-6(1) 7-5 6-2 | H2H | 5 | 175 | 11 | 12 | 50.6% | 69.5% | 33.8% | 16/26 |
| 1996-09-09 | Bournemouth | Clay | R32 | 16 | Felix Mantilla (2) | 256 | Luke Milligan | 6-4 6-1 | H2H | 3 | 65 | 0 | 1 | 75.6% | 73.5% | 54.5% | 0/1 |
| 1996-07-12 | Davis Cup G2 QF: GHA vs GBR | Hard | RR | 217 | Luke Milligan | - |  Isaac Donkor | 6-4 6-3 | H2H | 3 | - | - | - | - | - | - | - |
| 1996-07-12 | Davis Cup G2 QF: GHA vs GBR | Hard | RR | 217 | Luke Milligan | 513 | Frank Ofori | 6-1 3-6 6-4 6-2 | H2H | 5 | - | - | - | - | - | - | - |
| 1996-06-24 | Wimbledon | Grass | R32 | 62 | Tim Henman | 278 | Luke Milligan (WC) | 6-1 6-3 6-4 | H2H | 5 | 152 | 29 | 6 | 59.1% | 80.0% | 75.6% | 3/5 |
