Leonardo Silva defeated Rodrigo Pena 6-1 6-1 in the Bolivia F1 round of 16 on clay. The result followed the form book — Leonardo Silva came in leading the head-to-head 1–0. Leonardo Silva extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-14 | Mexico F4 | R16 | hard | Leonardo Silva | 3-6 6-3 6-1 |