Alexandre Simoni defeated Leonardo Silva 6-2 6-3 in the Cuba Mexico Masters 3 round of 32 on hard. The result followed the form book — Alexandre Simoni came in leading the head-to-head 2–0. Alexandre Simoni extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-17 | Chile F2 | R32 | clay | Alexandre Simoni | 2-6 7-6 6-2 |
| 1999-05-03 | Argentina F3 | R16 | clay | Alexandre Simoni | 6-1 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.