Simon Freund defeated Obrad Markovski 6-4 6-2 in the M25 Skopje 1 round of 32 on clay. The result followed the form book — Simon Freund came in leading the head-to-head 1–0. Simon Freund extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2021-08-25 | M15 Bratislava 4 | R32 | clay | Simon Freund | 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.