Nicolas Kiefer defeated Tim Henman 4-6 7-6 6-2 in the Toulouse round of 16 on hard. The upset overturned the form book — Tim Henman came in leading the head-to-head 7–1. Nicolas Kiefer narrowed the head-to-head to 7–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-02-14 | Rotterdam | R32 | hard | Tim Henman | 7-5 6-4 |
| 2004-08-30 | US Open | R16 | hard | Tim Henman | 6-7(5) 6-3 6-1 6-7(4) 3-0 RET |
| 2002-05-20 | Dusseldorf | RR | clay | Tim Henman | 7-6(6) 6-3 |
| 2002-02-18 | Rotterdam | R32 | hard | Tim Henman | 6-2 6-2 |
| 2001-08-06 | Cincinnati Masters | R16 | hard | Tim Henman | 7-5 6-3 |
| 2000-10-02 | Hong Kong | SF | hard | Nicolas Kiefer | 6-4 6-2 |
| 1999-08-09 | Cincinnati Masters | R16 | hard | Tim Henman | 6-4 6-1 |
| 1998-10-05 | Basel | QF | hard | Tim Henman | 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.