Paulo Carvallo defeated Oscar Rodriguez Arg 6-2 6-4 in the Chile 1 Masters 2 round of 32 on clay. The upset overturned the form book — Oscar Rodriguez Arg came in leading the head-to-head 2–0. Paulo Carvallo claimed a first win over Oscar Rodriguez Arg in three meetings, narrowing 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 |
| 1998-05-02 | Chile 2 Masters 3 | R32 | clay | Oscar Rodriguez Arg | 6-2 6-1 |