Todor Enev defeated Evgueni Smirnov 6-2 6-1 in the Macedonia F2 round of 16 on clay. The upset overturned the form book — Evgueni Smirnov came in leading the head-to-head 1–0, but Todor Enev had been the form player, winning 2 of their last 4 on clay. Todor Enev claimed a first win over Evgueni Smirnov in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-05-09 | Uzbekistan F4 | R32 | hard | Evgueni Smirnov | 7-6(8) 3-6 6-2 |