Alexandros Jakupovic defeated Richard Ruckelshausen 6-1 6-2 in the South Africa F1 round of 16 on hard. The result followed the form book — Alexandros Jakupovic came in leading the head-to-head 1–0. Alexandros Jakupovic extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-09-22 | Bosnia & Herzegovina F6 | R32 | clay | Alexandros Jakupovic | 6-2 4-6 6-4 |