Alexandros Jakupovic defeated Daniel Smethurst 6-3 6-1 in the Romania F4 round of 32 on clay. The upset overturned the form book — Daniel Smethurst came in leading the head-to-head 1–0. Alexandros Jakupovic claimed a first win over Daniel Smethurst in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-05-18 | Romania F3 | SF | clay | Daniel Smethurst | 4-6 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.