Leonardo Silva defeated Leandro Rosa 6-2 6-0 in the Brazil F3 round of 16 on hard. Leonardo Silva extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-20 | Bolivia F1 | R32 | clay | Leonardo Silva | 3-6 6-3 7-6 |
| 1999-07-26 | Uruguay F2 | R16 | clay | Leandro Rosa | 6-2 6-2 |