Dimana Krastevitch advanced when Radoslava Topalova retired 2-4 2-4 4-1 4-1 in the Sofia 10K qualifying round. Dimana Krastevitch claimed a first win over Radoslava Topalova in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-04 | Sofia 10K | QF | clay | Radoslava Topalova | 6-3 6-2 |