Chris Klingemann advanced when Daniel Garza retired 7-6 6-6 in the Mexico F8 round of 16. Chris Klingemann extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-07-21 | USA F19 | R16 | hard | Chris Klingemann | 7-6(4) 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.