Tim Henman defeated Stefan Koubek 6-4 6-1 in the Estoril round of 32 on clay. The upset overturned the form book — Stefan Koubek came in leading the head-to-head 3–2. Tim Henman narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-01-30 | Zagreb | SF | hard | Stefan Koubek | 6-3 3-6 6-2 |
| 2004-09-24 | Davis Cup WG PO: AUT vs GBR | RR | clay | Stefan Koubek | 6-3 6-3 6-1 |
| 2003-04-28 | Munich | R16 | clay | Stefan Koubek | 6-4 6-0 |
| 2000-03-06 | Scottsdale | R32 | hard | Tim Henman | 6-3 7-6(3) |
| 1999-11-08 | Stockholm | R32 | hard | Tim Henman | 6-1 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.