Ladislav Simon defeated Markus Krenn 6-3 6-3 in the Slovak Rep Masters 1 round of 16 on clay. The upset overturned the form book — Markus Krenn came in leading the head-to-head 1–0. Ladislav Simon claimed a first win over Markus Krenn in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-21 | Slovak Rep Masters 4 | F | clay | Markus Krenn | 6-2 6-2 |