Todor Enev defeated Dimitar Grabuloski 6-3 6-2 in the Macedonia F3 round of 32 on hard. The upset overturned the form book — Dimitar Grabuloski came in leading the head-to-head 1–0. Todor Enev claimed a first win over Dimitar Grabuloski in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-08-31 | Bulgaria F7 | R16 | clay | Dimitar Grabuloski | 3-6 6-1 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.