Laura Pena defeated Ludmila Richterova 6-4 6-3 in the Oporto 25K round of 32 on clay. The upset overturned the form book — Ludmila Richterova came in leading the head-to-head 1–0. Laura Pena claimed a first win over Ludmila Richterova in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-21 | Gorizia 25K | R32 | clay | Ludmila Richterova | 2-6 6-1 6-4 |