| 2002-06-24 | Wimbledon | Grass | R64 | 27 |  Nicolas Lapentti (22) | 251 |  Barry Cowan (WC) | 4-6 6-4 6-3 6-2 | H2H | 5 | 146 | 11 | 6 | 50.0% | 88.7% | 50.9% | 3/6 |
| 2002-06-24 | Wimbledon | Grass | R128 | 251 | Barry Cowan (WC) | 69 |  Attila Savolt | 6-7(3) 6-3 6-3 6-3 | H2H | 5 | 144 | 16 | 3 | 70.0% | 81.8% | 63.6% | 2/2 |
| 2001-10-01 | Tokyo | Hard | R64 | 314 |  Danai Udomchoke (Q) | 204 | Barry Cowan | 6-2 4-6 6-3 | H2H | 3 | 101 | 5 | 2 | 58.8% | 78.0% | 51.4% | 2/4 |
| 2001-09-21 | Davis Cup WG PO: ECU vs GBR | Clay | RR | 567 | Luis Adrian Morejon | 196 | Barry Cowan | 6-1 6-4 | H2H | 3 | - | - | - | - | - | - | - |
| 2001-06-25 | Wimbledon | Grass | R64 | 6 |  Pete Sampras (1) | 265 | Barry Cowan (WC) | 6-3 6-2 6-7(5) 4-6 6-3 | H2H | 5 | 171 | 26 | 7 | 69.6% | 81.3% | 66.7% | 3/5 |
| 2001-06-25 | Wimbledon | Grass | R128 | 265 | Barry Cowan (WC) | 383 | Mark Hilton (WC) | 6-3 6-2 7-6(2) | H2H | 5 | 116 | 18 | 7 | 63.8% | 76.1% | 44.7% | 6/8 |
| 2001-06-18 | Nottingham | Grass | R32 | 85 |  Mikhail Youzhny | 248 | Barry Cowan (Q) | 6-3 6-4 | H2H | 3 | 66 | 1 | 3 | 62.7% | 81.1% | 50.0% | 4/5 |
| 2000-11-20 | Brighton | Hard | R16 | 67 |  Davide Sanguinetti (7) | 171 | Barry Cowan | 6-4 6-3 | H2H | 3 | 72 | 4 | 5 | 62.1% | 77.8% | 36.4% | 1/3 |
| 2000-11-20 | Brighton | Hard | R32 | 171 | Barry Cowan | 181 | Martin Lee (WC) | 7-6(1) 6-4 | H2H | 3 | 96 | 6 | 5 | 55.1% | 81.4% | 51.4% | 6/7 |
| 2000-10-09 | Tokyo | Hard | R64 | 91 |  Sergi Bruguera | 171 | Barry Cowan (LL) | 6-4 6-3 | H2H | 3 | 67 | 3 | 2 | 66.7% | 72.7% | 63.6% | 6/6 |
