Roberto Menendez defeated Ivo Bratanov 6-4 6-1 in the Bulgaria 1 3 round of 32 on clay. The result followed the form book — Roberto Menendez came in leading the head-to-head 1–0. Roberto Menendez extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-08 | Bulgaria 1 2 | R16 | clay | Roberto Menendez | 7-6(4) 4-6 6-1 |