David Diaz Ventura advanced when Alexandros Jakupovic retired 6-3 3-2 in the Spain F12 round of 16. David Diaz Ventura claimed a first win over Alexandros Jakupovic in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-06-02 | Spain F22 | R32 | carpet | Alexandros Jakupovic | 3-2 |
| 2008-03-10 | Spain F10 | QF | clay | Alexandros Jakupovic | 6-1 6-2 |