Obrad Markovski defeated Kalin Ivanovski 3-6 6-4 6-4 in the M15 Skopje 2 round of 32 on clay. The upset overturned the form book — Kalin Ivanovski came in leading the head-to-head 1–0. Obrad Markovski claimed a first win over Kalin Ivanovski in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2020-03-08 | M15 Porec 1 | Q64 | clay | Kalin Ivanovski | 6-3 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.