Leonardo Silva defeated Leandro Rosa 3-6 6-3 7-6 in the Bolivia F1 round of 32 on clay. Leonardo Silva extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-26 | Uruguay F2 | R16 | clay | Leandro Rosa | 6-2 6-2 |
| 1998-11-02 | Brazil F3 | R16 | hard | Leonardo Silva | 6-2 6-0 |