Todor Enev defeated Tihomir Grozdanov 6-4 6-2 in the Bulgaria F7 qualifying round on clay. Todor Enev extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-05-03 | Bulgaria F1 | R32 | clay | Tihomir Grozdanov | 6-3 4-6 6-2 |
| 2006-08-21 | Bulgaria F1 | QF | clay | Todor Enev | 6-1 6-1 |