Dimitar Grabuloski defeated Todor Enev 3-6 6-1 6-3 in the Bulgaria F7 round of 16 on clay. The upset overturned the form book — Todor Enev came in leading the head-to-head 1–0. Dimitar Grabuloski claimed a first win over Todor Enev in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-06-25 | Macedonia F3 | R32 | hard | Todor Enev | 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.