Laura Pena defeated Maria Paola Zavagli 6-4 6-1 in the Cagliari 25K round of 32 on clay. The upset overturned the form book — Maria Paola Zavagli came in leading the head-to-head 1–0, but Laura Pena had been the form player, winning 5 of their last 8 on clay. Laura Pena claimed a first win over Maria Paola Zavagli in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-07 | Galatina 10K | R32 | clay | Maria Paola Zavagli | 6-4 6-3 |