Sergio Cortes defeated Juan Robinson Gamonal 6-3 7-5 in the Chile 2 Masters 4 round of 32 on clay. The result followed the form book — Sergio Cortes came in leading the head-to-head 2–1. Sergio Cortes extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-03-23 | Chile 1 Masters 2 | QF | clay | Juan Robinson Gamonal | 4-6 7-5 7-6 |
| 1996-03-23 | Chile 1 Masters 4 | R16 | clay | Sergio Cortes | 4-6 6-1 7-6 |
| 1995-09-30 | Chile Masters 3 | R32 | clay | Sergio Cortes | 6-2 6-1 |