Predrag Rusevski defeated Darko Madjarovski 0-6 7-6 6-4 in the Serbia F2 qualifying round on clay. The upset overturned the form book — Darko Madjarovski came in leading the head-to-head 2–1. Predrag Rusevski narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-09-12 | Belarus F2 | R16 | hard | Predrag Rusevski | 6-1 6-0 |
| 2005-09-05 | Belarus F1 | SF | clay | Darko Madjarovski | 5-7 6-4 6-2 |
| 2001-04-23 | Bulgaria 2 | R16 | clay | Darko Madjarovski | 7-6(1) 4-0 |