Federico Cavallero defeated Diego Cristin 7-5 6-3 in the Argentina F1 qualifying round on clay. The upset overturned the form book — Diego Cristin came in leading the head-to-head 1–0, but Federico Cavallero had been the form player, winning 6 of their last 10 on clay. Federico Cavallero claimed a first win over Diego Cristin in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-09-01 | Argentina F9 | R32 | clay | Diego Cristin | 7-5 2-6 6-2 |