Karol Kucera defeated Richard Krajicek 7-6 6-4 in the New Haven semi-final on hard. The upset overturned the form book — Richard Krajicek came in leading the head-to-head 1–0, defending last year's quarter-final. Karol Kucera claimed a first win over Richard Krajicek in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-22 | London | QF | carpet | Richard Krajicek | 6-1 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 193). ATP, WTA & Challenger.