Yordan Kanev defeated Ilia Kushev 6-4 6-7 7-6 in the Bulgaria 1 4 qualifying round on clay. The upset overturned the form book — Ilia Kushev came in leading the head-to-head 5–2. Yordan Kanev narrowed the head-to-head to 5–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-05-12 | Bulgaria F2 | R32 | clay | Yordan Kanev | 7-5 |
| 2007-08-27 | Bulgaria F6 | R32 | clay | Ilia Kushev | 6-3 6-0 |
| 2006-06-19 | Serbia & Montenegro F1 | SF | clay | Yordan Kanev | 4-6 7-6(2) 6-3 |
| 2006-06-12 | Macedonia F2 | R32 | clay | Ilia Kushev | 6-2 6-2 |
| 2004-05-03 | Bulgaria 1 4 | F | clay | Ilia Kushev | 4-6 6-4 7-5 |
| 2004-05-03 | Bulgaria 1 3 | SF | clay | Ilia Kushev | 6-1 3-6 6-2 |
| 2003-10-13 | Greece F4 | SF | clay | Ilia Kushev | 7-6(2) 6-0 |