Vjekoslav Skenderovic defeated Jurgen Zopp 6-4 6-4 in the Portugal F4 round of 32 on hard. The upset overturned the form book — Jurgen Zopp came in leading the head-to-head 1–0. Vjekoslav Skenderovic claimed a first win over Jurgen Zopp in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-02-16 | Croatia F2 | R32 | hard | Jurgen Zopp | 6-1 4-6 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.