T. Radovanovic defeated Simon Knezevic 7-6 6-2 in the M25 Skopje q64 on clay. The upset overturned the form book — Simon Knezevic came in leading the head-to-head 1–0. T. Radovanovic claimed a first win over Simon Knezevic in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-05-26 | M15 Kursumlijska Banja 5 | Q32 | clay | Simon Knezevic | 6-4 6-3 |