Tim Henman defeated Yevgeny Kafelnikov 6-4 6-4 in the Tour Finals round robin on hard. The upset overturned the form book — Yevgeny Kafelnikov came in leading the head-to-head 5–4. Tim Henman narrowed the head-to-head to 5–5.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-05-20 | Dusseldorf | RR | clay | Tim Henman | 6-2 7-6(6) |
| 2000-08-14 | Indianapolis | QF | hard | Tim Henman | 7-6(4) 6-2 |
| 2000-02-14 | Rotterdam | SF | hard | Tim Henman | 6-3 4-6 6-3 |
| 1999-08-09 | Cincinnati Masters | QF | hard | Yevgeny Kafelnikov | 7-5 7-5 |
| 1999-02-15 | Rotterdam | F | hard | Yevgeny Kafelnikov | 6-2 7-6(3) |
| 1998-11-02 | Paris Masters | R16 | hard | Yevgeny Kafelnikov | 6-3 6-7(5) 7-6(2) |
| 1998-09-14 | Tashkent | F | hard | Tim Henman | 7-5 6-4 |
| 1998-02-23 | London | QF | carpet | Yevgeny Kafelnikov | 4-6 6-4 6-2 |
| 1997-08-11 | New Haven | QF | hard | Yevgeny Kafelnikov | 5-7 6-3 6-4 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (200 vs 200). ATP, WTA & Challenger.