Radoslava Topalova defeated Anna Koumantou 1-6 6-3 6-2 in the Volos 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 |
|---|---|---|---|---|---|
| 1999-08-23 | Skiathos 10K | R32 | clay | Radoslava Topalova | 0-6 6-2 6-2 |