Matias Silva defeated Brett Ross 6-4 2-6 6-4 in the Peru F3 round of 16 on clay. The upset overturned the form book — Brett Ross came in leading the head-to-head 1–0, but Matias Silva had been the form player, winning 4 of their last 8 on clay. Matias Silva claimed a first win over Brett Ross in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-07-07 | Peru F2 | R16 | clay | Brett Ross | 6-2 6-4 |