Ivaylo Traykov defeated Simeon Ivanov 6-2 6-2 in the Bulgaria 1 1 round of 16 on clay. The result followed the form book — Ivaylo Traykov came in leading the head-to-head 4–0. Ivaylo Traykov extended the head-to-head to 5–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-09-01 | Bulgaria F7 | QF | clay | Ivaylo Traykov | 6-3 7-5 |
| 2008-08-25 | Bulgaria F6 | QF | clay | Ivaylo Traykov | 7-6(3) 6-3 |
| 2008-05-05 | Bulgaria F1 | F | clay | Ivaylo Traykov | 6-1 6-2 |
| 2007-09-03 | Bulgaria F7 | SF | clay | Ivaylo Traykov | 6-1 6-1 |