Ljiljana Nanusevic defeated Biljana Pawlowa Dimitrova 6-4 6-3 in the Skopje 10K round of 32 on clay. The result followed the form book — Ljiljana Nanusevic came in leading the head-to-head 1–0. Ljiljana Nanusevic extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-04 | Sofia 10K | R32 | clay | Ljiljana Nanusevic | 6-3 4-6 6-3 |