Sergio Cortes defeated Oscar Rodriguez Arg 6-3 6-4 in the Chile Masters 1 qualifying round on clay. The result followed the form book — Sergio Cortes came in leading the head-to-head 1–0. Sergio Cortes extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-10-05 | Chile 2 Masters 3 | R32 | clay | Sergio Cortes | 3-6 6-2 7-6 |