Oana Elena Golimbioschi defeated Gabriela Kucerova 7-5 7-6 in the San Severo 10K round of 16 on clay. The upset overturned the form book — Gabriela Kucerova came in leading the head-to-head 1–0. Oana Elena Golimbioschi claimed a first win over Gabriela Kucerova in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-27 | Mallorca 10K | F | clay | Gabriela Kucerova | 6-1 6-2 |