Richard Krajicek defeated Yevgeny Kafelnikov 6-4 6-4 in the New Haven semi-final on hard. The upset overturned the form book — Yevgeny Kafelnikov came in leading the head-to-head 4–3, defending last year's semi-final. Richard Krajicek narrowed the head-to-head to 4–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-07 | Cincinnati Masters | R64 | hard | Yevgeny Kafelnikov | 6-3 1-6 6-3 |
| 1999-08-30 | US Open | QF | hard | Yevgeny Kafelnikov | 7-6 7-6 3-6 1-6 7-6 |
| 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 |
| 1996-05-27 | Roland Garros | QF | clay | Yevgeny Kafelnikov | 6-3 6-4 6-7(4) 6-2 |
| 1994-05-02 | Hamburg | QF | clay | Yevgeny Kafelnikov | 6-3 6-2 |
Averages over each player's completed matches in the selected window (200 vs 200). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About