Simeon Ivanov defeated Predrag Rusevski 0-6 7-5 7-5 in the Bulgaria 1 3 round of 32 on clay. The upset overturned the form book — Predrag Rusevski came in leading the head-to-head 2–0. Simeon Ivanov claimed a first win over Predrag Rusevski in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-05-25 | Bulgaria F4 | R16 | clay | Predrag Rusevski | 6-3 6-0 |
| 2006-05-01 | Bulgaria 1 2 | R16 | clay | Predrag Rusevski | 6-1 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.