| 31‑Jul‑2006 | Washington | Hard | R16 | 64 | 503 | (14)Henman d. (LL)Jan Michael Gambill [USA] | 6-1 6-3 | | 1.52 | 13.5% | 0.0% | 55.8% | 75.9% | 52.2% | 4/5 | 1:13 |
| 12‑May‑2003 | Hamburg Masters | Clay | R64 | 27 | 40 | Henman d. Jan Michael Gambill [USA] | 7-5 6-4 | | 1.42 | 6.8% | 1.7% | 71.2% | 66.7% | 76.5% | 0/2 | 1:29 |
| 10‑Mar‑2003 | Indian Wells Masters | Hard | R64 | 13 | 35 | (13)Henman d. Jan Michael Gambill [USA] | 7-5 6-2 | | 1.71 | 5.0% | 5.0% | 65.0% | 84.6% | 52.4% | 1/1 | 1:35 |
| 6‑Aug‑2001 | Cincinnati Masters | Hard | QF | 8 | 22 | (7)Henman d. Jan Michael Gambill [USA] | 4-6 6-2 6-2 | | 1.26 | 2.2% | 3.2% | 57.0% | 62.3% | 57.5% | 10/13 | 2:23 |
| 8‑Nov‑1999 | Stockholm | Hard | R16 | 10 | 71 | Jan Michael Gambill [USA] d. (2)Henman | 7-5 6-3 | | 0.64 | 8.7% | 7.2% | 49.3% | 82.4% | 34.3% | 4/7 | 1:18 |
| 26‑Oct‑1998 | Stuttgart Masters | Hard | R16 | 9 | | Jan Michael Gambill [USA] d. (9)Henman | 7-6(2) 1-6 7-6(5) | | 1.12 | 24.3% | 7.8% | 53.4% | 83.6% | 50.0% | 7/8 | 2:14 |
| 13‑Apr‑1998 | Tokyo | Hard | QF | 15 | 81 | (11)Jan Michael Gambill [USA] d. (3)Henman | 6-3 4-6 6-3 | | 0.91 | 10.7% | 9.5% | 46.4% | 82.1% | 31.1% | 5/11 | 1:45 |