Leonardo Silva defeated Eduardo Bergmann 7-5 7-6 in the Brazil 3 Masters 3 round of 32 on hard. 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 |
|---|---|---|---|---|---|
| 1999-11-22 | Brazil F1 | R32 | clay | Leonardo Silva | 3-6 6-4 6-3 |