Chris Klingemann defeated Luigi Dagord 7-6 7-6 in the Mexico F7 round of 16 on hard. The upset overturned the form book — Luigi Dagord came in leading the head-to-head 1–0. Chris Klingemann claimed a first win over Luigi Dagord in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-05-19 | Mexico F8 | QF | hard | Luigi Dagord | 6-1 6-4 |