Radoslava Topalova defeated Dina Milosevic 6-4 4-6 7-6 in the Skopje 10K round of 32 on clay. The result followed the form book — Radoslava Topalova came in leading the head-to-head 1–0. Radoslava Topalova extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-25 | Kastoria 10K | R16 | carpet | Radoslava Topalova | 6-1 6-3 |