Pete Sampras defeated Richard Krajicek 4-6 7-6 6-4 6-2 in the US Open quarter-final on hard. The upset overturned the form book — Richard Krajicek came in leading the head-to-head 3–1, defending last year's quarter-final. Pete Sampras narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-09 | Cincinnati Masters | QF | hard | Pete Sampras | 6-4 6-2 |
| 1999-03-15 | Miami Masters | QF | hard | Richard Krajicek | 6-2 7-6(6) |
| 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 (143 vs 73). ATP, WTA & Challenger.