Leonardo Silva advanced when Flavio Saretta retired 7-6 3-2 in the Brazil F3 qualifying round. Leonardo Silva claimed a first win over Flavio Saretta in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-29 | Brazil F2 | R16 | clay | Flavio Saretta | 4-6 6-4 7-5 |
| 1999-05-31 | Mexico F2 | QF | hard | Flavio Saretta | 0-6 6-2 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.