Martin Stepanek defeated Petr Kovacka 6-1 3-6 6-1 in the Czech Republic Masters 1 round of 16 on hard. Martin Stepanek extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-25 | Czech Republic Masters 3 | SF | carpet | Petr Kovacka | 3-6 6-3 7-6 |
| 1999-10-25 | Czech Republic Masters 4 | QF | carpet | Martin Stepanek | 6-2 6-2 |