Yevgeny Kafelnikov defeated Richard Krajicek 6-3 1-6 6-3 in the Cincinnati Masters round of 64 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. Yevgeny Kafelnikov narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-30 | US Open | QF | hard | Yevgeny Kafelnikov | 7-6(0) 7-6(4) 3-6 1-6 7-6(5) |
| 1998-10-26 | Stuttgart Masters | F | carpet | Richard Krajicek | 6-4 6-3 6-3 |
| 1998-08-03 | Canada Masters | QF | hard | Richard Krajicek | 6-4 6-4 |
| 1998-05-11 | Rome Masters | R16 | clay | Richard Krajicek | 6-2 3-6 7-6(6) |
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 73). ATP, WTA & Challenger.