Jan Siemerink defeated Richard Krajicek 6-4 4-6 6-4 in the Rotterdam semi-final on hard. The upset overturned the form book — Richard Krajicek came in leading the head-to-head 4–1, defending the title. Jan Siemerink narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-03-15 | Miami Masters | R32 | hard | Richard Krajicek | 6-3 6-2 |
| 1999-03-08 | Indian Wells Masters | R16 | hard | Richard Krajicek | 6-4 6-4 |
| 1996-08-12 | New Haven | QF | hard | Jan Siemerink | 7-6(3) 6-2 |
| 1995-02-27 | Rotterdam | R16 | hard | Richard Krajicek | 7-5 6-4 |
| 1994-08-29 | US Open | R128 | hard | Richard Krajicek | 7-6(2) 6-4 6-7(2) 6-7(8) 6-4 |
Averages over each player's completed matches in the selected window (151 vs 191). 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