Darko Madjarovski advanced when Predrag Rusevski retired 7-6 4-0 in the Bulgaria 2 round of 16. Darko Madjarovski narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-08 | Serbia F2 | QF | clay | Predrag Rusevski | 0-6 7-6(3) 6-4 |
| 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 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.