Gabriel Keymer defeated Alexandre Simoni 6-3 6-2 in the Brazil 1 Masters 1 round of 32 on clay. Gabriel Keymer extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-24 | Chile F3 | R16 | clay | Gabriel Keymer | 6-3 2-6 6-4 |
| 1999-05-10 | Chile F1 | SF | clay | Alexandre Simoni | 6-1 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.