Oscar Rodriguez Arg defeated Paulo Carvallo 6-2 6-1 in the Chile 2 Masters 3 round of 32 on clay. Oscar Rodriguez Arg extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-10 | Chile F1 | R16 | clay | Oscar Rodriguez Arg | 6-4 6-2 |
| 1999-04-10 | Chile 1 Masters 2 | R32 | clay | Paulo Carvallo | 6-2 6-4 |