Alexandros Jakupovic defeated David Canudas Fernandez 6-1 6-4 in the Spain F9 round of 16 on clay. The upset overturned the form book — David Canudas Fernandez came in leading the head-to-head 1–0. Alexandros Jakupovic claimed a first win over David Canudas Fernandez in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-05-12 | Greece F2 | R16 | carpet | David Canudas Fernandez | 4-6 6-3 7-5 |