Luigi Dagord defeated Chris Klingemann 6-1 6-4 in the Mexico F8 qualifying round on hard. The upset overturned the form book — Chris Klingemann came in leading the head-to-head 1–0, but Luigi Dagord had been the form player, winning 5 of their last 6 on hard. Luigi Dagord claimed a first win over Chris Klingemann in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-05-12 | Mexico F7 | R16 | hard | Chris Klingemann | 7-6(4) 7-6(8) |