Chris Klingemann defeated Adam Thompson 6-2 6-3 in the USA F19 round of 32 on hard. The upset overturned the form book — Adam Thompson came in leading the head-to-head 1–0, but Chris Klingemann had been the form player, winning 4 of their last 6 on hard. Chris Klingemann claimed a first win over Adam Thompson in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-05-25 | Mexico F7 | QF | hard | Adam Thompson | 3-6 6-1 6-2 |