Martin Stepanek defeated Leos Friedl 6-4 7-6 in the s Hertogenbosch qualifying round of 16 on grass. The upset overturned the form book — Leos Friedl came in leading the head-to-head 2–0. Martin Stepanek claimed a first win over Leos Friedl in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-25 | Czech Republic Masters 1 | SF | carpet | Leos Friedl | 6-3 6-4 |
| 1997-10-20 | Czech Republic Masters 3 | QF | carpet | Leos Friedl | 5-7 7-6 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.