Tim Henman defeated Pete Sampras 6-3 6-4 in the Cincinnati Masters round of 16 on hard. The upset overturned the form book — Pete Sampras came in leading the head-to-head 4–0, defending the title. Tim Henman claimed a first win over Pete Sampras in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-21 | Wimbledon | SF | grass | Pete Sampras | 3-6 6-4 6-3 6-4 |
| 1999-06-07 | Queen's Club | F | grass | Pete Sampras | 6-7(1) 6-4 7-6(4) |
| 1998-10-12 | Vienna | QF | hard | Pete Sampras | 6-0 6-3 |
| 1998-06-22 | Wimbledon | SF | grass | Pete Sampras | 6-3 4-6 7-5 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 143). ATP, WTA & Challenger.