German Gaich defeated Federico Sansonetti 7-6 2-6 6-4 in the Chile F5 round of 32 on clay. The upset overturned the form book — Federico Sansonetti came in leading the head-to-head 1–0. German Gaich claimed a first win over Federico Sansonetti in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-09-29 | Argentina F11 | R16 | clay | Federico Sansonetti | 6-7(5) 6-2 7-6(8) |