Sjeng Schalken defeated Jim Courier 6-4 7-6 in the Moscow round of 16 on hard. The upset overturned the form book — Jim Courier came in leading the head-to-head 4–0, but Sjeng Schalken had been the form player, winning 2 of their last 4 on hard. Sjeng Schalken claimed a first win over Jim Courier in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-21 | Wimbledon | R32 | grass | Jim Courier | 7-6 3-6 3-6 7-5 13-11 |
| 1997-01-13 | Australian Open | R128 | hard | Jim Courier | 6-7 6-3 4-6 6-1 8-6 |
| 1997-01-01 | Doha | R32 | hard | Jim Courier | 7-6(10) 7-5 |
| 1996-12-30 | Doha | R32 | hard | Jim Courier | 7-6 7-5 |
Averages over each player's completed matches in the selected window (200 vs 147). 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