Todor Enev defeated Simeon Ivanov 6-2 6-1 in the Bulgaria F5 qualifying round on clay. The result followed the form book — Todor Enev came in leading the head-to-head 3–1. Todor Enev extended the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-02-25 | India F2 | R16 | hard | Simeon Ivanov | 6-3 6-0 |
| 2007-03-12 | Israel F2 | R16 | hard | Todor Enev | 6-1 6-0 |
| 2007-01-29 | India F2 | R16 | hard | Todor Enev | 6-2 6-1 |
| 2006-09-04 | Bulgaria F3 | R16 | clay | Todor Enev | 1-6 6-4 6-1 |