Radoslava Topalova defeated Dina Milosevic 6-1 6-3 in the Kastoria 10K round of 16 on carpet. 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 |
|---|---|---|---|---|---|
| 1999-09-27 | Skopje 10K | R32 | clay | Radoslava Topalova | 6-4 4-6 7-6 |