Radoslava Topalova defeated Dimana Krastevitch 6-3 6-2 in the Sofia 10K qualifying round on clay. The upset overturned the form book — Dimana Krastevitch came in leading the head-to-head 1–0. Radoslava Topalova claimed a first win over Dimana Krastevitch in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-09 | Sofia 10K | QF | clay | Dimana Krastevitch | 2-4 2-4 4-1 4-1 |