Gustavo Kuerten defeated Tim Henman 3-6 6-1 7-5 in the Indianapolis quarter-final on hard. The upset overturned the form book — Tim Henman came in leading the head-to-head 5–2, defending last year's semi-final. Gustavo Kuerten narrowed the head-to-head to 5–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-05-02 | Rome Masters | R64 | clay | Tim Henman | 6-3 6-3 |
| 2004-07-26 | Canada Masters | R32 | hard | Gustavo Kuerten | 7-5 6-4 |
| 2003-10-27 | Paris Masters | R16 | hard | Tim Henman | 6-4 6-2 |
| 2002-08-05 | Cincinnati Masters | R64 | hard | Tim Henman | 6-3 6-4 |
| 2001-08-06 | Cincinnati Masters | SF | hard | Gustavo Kuerten | 6-2 1-6 7-6(4) |
| 2000-08-07 | Cincinnati Masters | SF | hard | Tim Henman | 6-7(11) 6-3 7-6(0) |
| 1998-03-16 | Miami Masters | QF | hard | Tim Henman | 6-2 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.