Nicolas Massu defeated Tim Henman 3-6 7-5 6-2 in the Adelaide semi-final on hard. The upset overturned the form book — Tim Henman came in leading the head-to-head 5–0, defending last year's quarter-final. Nicolas Massu claimed a first win over Tim Henman in six meetings, narrowing the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-08-15 | Cincinnati Masters | R64 | hard | Tim Henman | 6-2 6-1 |
| 2005-05-02 | Rome Masters | R32 | clay | Tim Henman | 6-3 6-2 |
| 2004-04-19 | Monte Carlo Masters | R16 | clay | Tim Henman | 3-6 6-4 6-3 |
| 2002-08-12 | Indianapolis | R32 | hard | Tim Henman | 6-3 1-6 7-5 |
| 2002-04-15 | Monte Carlo Masters | R32 | clay | Tim Henman | 6-1 7-6(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 200). ATP, WTA & Challenger.