Alejandro Olivera defeated Rodrigo Ribeiro 6-3 7-6 in the Brazil F4 round of 32 on clay. The result followed the form book — Alejandro Olivera came in leading the head-to-head 1–0. Alejandro Olivera extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-29 | Brazil F2 | R32 | clay | Alejandro Olivera | 6-3 6-3 |