| 20‑May‑2002 | Dusseldorf | Clay | RR | 6 | 5 | Henman d. Yevgeny Kafelnikov [RUS] | 6-2 7-6(6) | | 1.08 | 2.9% | 2.9% | 53.6% | 64.9% | 68.8% | 1/2 | 1:26 |
| 14‑Aug‑2000 | Indianapolis | Hard | QF | 11 | 5 | (7)Henman d. (2)Yevgeny Kafelnikov [RUS] | 7-6(4) 6-2 | | 1.13 | 5.7% | 1.4% | 54.3% | 78.9% | 59.4% | 1/1 | 1:22 |
| 14‑Feb‑2000 | Rotterdam | Hard | SF | 11 | 2 | (5)Henman d. (1)Yevgeny Kafelnikov [RUS] | 6-3 4-6 6-3 | | 1.09 | 14.3% | 5.1% | 57.1% | 73.2% | 42.9% | 8/11 | 2:02 |
| 9‑Aug‑1999 | Cincinnati Masters | Hard | QF | 5 | 2 | (4)Yevgeny Kafelnikov [RUS] d. (5)Henman | 7-5 7-5 | | 0.82 | 14.1% | 5.6% | 56.3% | 70.0% | 54.8% | 5/8 | 1:25 |
| 15‑Feb‑1999 | Rotterdam | Carpet | F | 7 | 2 | (2)Yevgeny Kafelnikov [RUS] d. (3)Henman | 6-2 7-6(3) | | 0.83 | 10.5% | 10.5% | 43.9% | 64.0% | 40.6% | 1/5 | 1:27 |
| 2‑Nov‑1998 | Paris Masters | Carpet | R16 | 10 | 8 | (8)Yevgeny Kafelnikov [RUS] d. (9)Henman | 6-3 6-7(5) 7-6(2) | | 0.71 | 7.7% | 2.6% | 51.3% | 73.3% | 40.4% | 4/8 | 2:13 |
| 14‑Sep‑1998 | Tashkent | Hard | F | 11 | 10 | (2)Henman d. (1)Yevgeny Kafelnikov [RUS] | 7-5 6-4 | | 1.12 | 15.4% | 5.1% | 59.0% | 65.2% | 53.1% | 5/7 | 1:37 |
| 23‑Feb‑1998 | London | Carpet | QF | 21 | 7 | (3)Yevgeny Kafelnikov [RUS] d. Henman | 4-6 6-4 6-2 | | 0.89 | 17.3% | 5.1% | 52.0% | 74.5% | 38.3% | 6/10 | 2:00 |
| 10‑Nov‑1997 | Tour Finals | Hard | RR | 17 | 6 | Henman d. Yevgeny Kafelnikov [RUS] | 6-4 6-4 | | 1.27 | 19.0% | 1.7% | 43.1% | 92.0% | 51.5% | 1/2 | 1:08 |
| 11‑Aug‑1997 | New Haven | Hard | QF | 21 | 6 | (1)Yevgeny Kafelnikov [RUS] d. (7)Henman | 5-7 6-3 6-4 | | 1.02 | 19.3% | 2.3% | 52.3% | 78.3% | 47.6% | 3/6 | 1:59 |
| 30‑Sep‑1996 | Lyon | Carpet | SF | 32 | 5 | (2)Yevgeny Kafelnikov [RUS] d. Henman | 6-1 6-3 | | 0.53 | 8.8% | 3.5% | 45.6% | 50.0% | 51.6% | 3/7 | 0:58 |
| 5‑Aug‑1996 | Cincinnati Masters | Hard | R32 | 37 | 4 | (4)Yevgeny Kafelnikov [RUS] d. Henman | 6-4 6-4 | | 0.67 | 12.0% | 3.6% | 61.4% | 66.7% | 50.0% | 10/12 | 1:13 |
| 24‑Jun‑1996 | Wimbledon | Grass | R128 | 62 | 5 | Henman d. (5)Yevgeny Kafelnikov [RUS] | 7-6(6) 6-3 6-7(2) 4-6 7-5 | (ch) | 1.07 | 10.7% | 3.3% | 77.6% | 75.3% | 29.2% | 8/13 | 3:38 |
| 4‑Mar‑1996 | Rotterdam | Carpet | SF | 79 | 8 | (3)Yevgeny Kafelnikov [RUS] d. (Q)Henman | 7-6(4) 6-3 | | 0.93 | 16.1% | 3.6% | 57.1% | 78.1% | 45.8% | 0/3 | 1:22 |