Chris Klingemann advanced when David Souto retired 7-6 1-0 in the Venezuela F1 round of 32. Chris Klingemann claimed a first win over David Souto in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-06-23 | Venezuela F3 | R16 | hard | David Souto | 2-6 6-2 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.