Pete Sampras advanced when Jan Michael Gambill retired 4-1 in the Stuttgart Masters quarter-final. 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 |
| 1998-08-10 | Cincinnati Masters | R16 | hard | Pete Sampras | 7-6(3) 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.