Ivo Bratanov defeated Artemon Apostu Efremov 6-3 6-4 in the Macedonia F2 round of 16 on clay. The upset overturned the form book — Artemon Apostu Efremov came in leading the head-to-head 1–0. Ivo Bratanov claimed a first win over Artemon Apostu Efremov in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-24 | Bulgaria Masters 3 | R32 | clay | Artemon Apostu Efremov | 4-6 6-3 6-4 |