Alvaro Raposo De Oliveira defeated Guillermo Carry 6-4 6-1 in the Bolivia F4 round of 16 on clay. The upset overturned the form book — Guillermo Carry came in leading the head-to-head 2–0, but Alvaro Raposo De Oliveira had been the form player, winning 5 of their last 10 on clay. Alvaro Raposo De Oliveira claimed a first win over Guillermo Carry in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-09-22 | Bolivia F3 | R32 | clay | Guillermo Carry | 7-6(2) 6-0 |
| 2008-09-15 | Bolivia F2 | R32 | clay | Guillermo Carry | 6-2 6-1 |