Massimo Capone defeated Talal Ouahabi 6-3 6-2 in the Egypt F9 round of 16 on clay. The upset overturned the form book — Talal Ouahabi came in leading the head-to-head 1–0. Massimo Capone claimed a first win over Talal Ouahabi in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-01 | Egypt F8 | QF | clay | Talal Ouahabi | 6-4 6-2 |