Tim Henman defeated Daniel Vacek 6-3 5-7 6-1 in the Canada Masters quarter-final on hard. The result followed the form book — Tim Henman came in leading the head-to-head 3–1, defending last year's round of 64. Tim Henman extended the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-25 | Stuttgart Masters | R32 | carpet | Daniel Vacek | 6-3 6-1 |
| 1999-05-10 | Rome Masters | R64 | clay | Tim Henman | 7-5 6-3 |
| 1997-09-22 | Toulouse | R32 | hard | Tim Henman | 6-4 1-6 6-3 |
| 1997-08-11 | New Haven | R32 | hard | Tim Henman | 4-6 7-6(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 139). ATP, WTA & Challenger.