Martin Stepanek defeated Roman Smotlak 6-4 7-6 in the Czech Republic Masters 4 round of 16 on carpet. The upset overturned the form book — Roman Smotlak came in leading the head-to-head 1–0. Martin Stepanek claimed a first win over Roman Smotlak in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-05 | Austria F1 | F | clay | Roman Smotlak | 7-5 1-6 6-3 |