Tim Henman defeated Jan Michael Gambill 7-5 6-4 in the Hamburg Masters round of 64 on clay. Tim Henman extended the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-07-31 | Washington | R16 | hard | Tim Henman | 6-1 6-3 |
| 2003-03-10 | Indian Wells Masters | R64 | hard | Tim Henman | 7-5 6-2 |
| 2001-08-06 | Cincinnati Masters | QF | hard | Tim Henman | 4-6 6-2 6-2 |
| 1999-11-08 | Stockholm | R16 | hard | Jan Michael Gambill | 7-5 6-3 |
| 1998-10-26 | Stuttgart Masters | R16 | carpet | Jan Michael Gambill | 7-6(2) 1-6 7-6(5) |
| 1998-04-13 | Tokyo | QF | hard | Jan Michael Gambill | 6-3 4-6 6-3 |
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 99). ATP, WTA & Challenger.