Jose De Armas defeated Chris Klingemann 6-2 6-1 in the Delray Beach q32 on hard. The result followed the form book — Jose De Armas came in leading the head-to-head 1–0. Jose De Armas extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-06-09 | Venezuela F1 | R16 | hard | Jose De Armas | 2-6 6-2 7-6(3) |