Guillermo Olaso defeated Darko Madjarovski 6-4 6-3 in the Serbia F1 round of 32 on clay. The upset overturned the form book — Darko Madjarovski came in leading the head-to-head 1–0. Guillermo Olaso claimed a first win over Darko Madjarovski in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-06-25 | Serbia F2 | F | clay | Darko Madjarovski | 5-7 6-2 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.