Ivan Anhelov defeated Vasil Shandarov 6-4 6-4 in the M15 Kursumlijska Banja 4 q64 on clay. The upset overturned the form book — Vasil Shandarov came in leading the head-to-head 1–0, but Ivan Anhelov had been the form player, winning 1 of their last 8 on clay. Ivan Anhelov claimed a first win over Vasil Shandarov in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2023-10-01 | M25 Pazardzhik 2 | Q32 | clay | Vasil Shandarov | 6-3 2-6 10-4 |