Richard Krajicek defeated Pete Sampras 6-2 7-6 in the Miami Masters quarter-final on hard. The upset overturned the form book — Pete Sampras came in defending last year's round of 32. Richard Krajicek extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-28 | US Open | QF | hard | Pete Sampras | 4-6 7-6(6) 6-4 6-2 |
| 1999-08-09 | Cincinnati Masters | QF | hard | Pete Sampras | 6-4 6-2 |
| 1998-10-26 | Stuttgart Masters | SF | carpet | Richard Krajicek | 6-7(2) 6-4 7-6(5) |
| 1997-10-20 | Stuttgart Masters | R16 | carpet | Richard Krajicek | 6-4 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 (133 vs 190). ATP, WTA & Challenger.