Diego Cristin defeated Federico Cavallero 7-5 2-6 6-2 in the Argentina F9 round of 32 on clay. The upset overturned the form book — Federico Cavallero came in leading the head-to-head 1–0. Diego Cristin claimed a first win over Federico Cavallero in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-05-05 | Argentina F1 | QF | clay | Federico Cavallero | 7-5 6-3 |