Ludmila Richterova defeated Laura Pena 2-6 6-1 6-4 in the Gorizia 25K round of 32 on clay. The upset overturned the form book — Laura Pena came in leading the head-to-head 1–0. Ludmila Richterova claimed a first win over Laura Pena in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-27 | Oporto 25K | R32 | clay | Laura Pena | 6-4 6-3 |