Pete Sampras defeated Jan Michael Gambill 7-6 6-3 in the Cincinnati Masters round of 16 on hard. The result followed the form book — Pete Sampras came in leading the head-to-head 3–1, defending the title. Pete Sampras extended the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-06-11 | Queen's Club | QF | grass | Pete Sampras | 7-6(1) 7-5 |
| 2000-06-26 | Wimbledon | QF | grass | Pete Sampras | 6-4 6-7(4) 6-4 6-4 |
| 1999-03-01 | Scottsdale | R16 | hard | Jan Michael Gambill | 4-6 6-3 6-4 |
| 1998-10-26 | Stuttgart Masters | QF | carpet | Pete Sampras | 4-1 RET |
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.