Leos Friedl defeated Martin Stepanek 5-7 7-6 6-1 in the Czech Republic Masters 3 qualifying round on carpet. Leos Friedl extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-06-16 | s Hertogenbosch | Q16 | grass | Martin Stepanek | 6-4 7-6(4) |
| 1999-10-25 | Czech Republic Masters 1 | SF | carpet | Leos Friedl | 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.