Leandro Rosa defeated Leonardo Silva 6-2 6-2 in the Uruguay F2 round of 16 on clay. The upset overturned the form book — Leonardo Silva came in leading the head-to-head 2–0. Leandro Rosa claimed a first win over Leonardo Silva in three meetings, narrowing 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 |
| 1998-11-02 | Brazil F3 | R16 | hard | Leonardo Silva | 6-2 6-0 |