Charly Villeneuve defeated Matt Simpson 6-4 7-5 in the Bulgaria F5 round of 16 on clay. The result followed the form book — Charly Villeneuve came in leading the head-to-head 1–0. Charly Villeneuve extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-08-27 | Bulgaria F6 | R16 | clay | Charly Villeneuve | 6-3 3-6 6-1 |