Jan Kroslak defeated Jan Siemerink 5-7 7-6 7-6 in the Moscow round of 32 on hard. The upset overturned the form book — Jan Siemerink came in leading the head-to-head 1–0. Jan Kroslak claimed a first win over Jan Siemerink in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-09 | Cincinnati Masters | R64 | hard | Jan Siemerink | 6-1 6-2 |
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 (56 vs 91). ATP, WTA & Challenger.