Plamen Milushev defeated Tihomir Grozdanov 7-5 6-7 6-3 in the Bulgaria F5 round of 32 on clay. The upset overturned the form book — Tihomir Grozdanov came in leading the head-to-head 1–0. Plamen Milushev claimed a first win over Tihomir Grozdanov in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2013-06-17 | Bulgaria F4 | R16 | clay | Tihomir Grozdanov | 6-4 6-1 |