Brett Ross defeated Matias Silva 6-2 6-4 in the Peru F2 round of 16 on clay. The upset overturned the form book — Matias Silva came in leading the head-to-head 1–0. Brett Ross claimed a first win over Matias Silva in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-07-14 | Peru F3 | R16 | clay | Matias Silva | 6-4 2-6 6-4 |