Filipa Gabrovska defeated Marina Petrovic 6-0 7-6 in the Skopje 10K round of 32 on clay. The result followed the form book — Filipa Gabrovska came in leading the head-to-head 1–0. Filipa Gabrovska extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-04 | Sofia 10K | R16 | clay | Filipa Gabrovska | 7-5 6-1 |