Juan Manuel Romanazzi defeated Bruno Tiberti 2-6 6-1 6-2 in the Uruguay F1 round of 32 on clay. The upset overturned the form book — Bruno Tiberti came in leading the head-to-head 1–0. Juan Manuel Romanazzi claimed a first win over Bruno Tiberti in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-12-08 | Argentina F18 | R16 | clay | Bruno Tiberti | 6-2 4-6 6-3 |