Sergio Cortes defeated Ruben Gajardo 3-6 6-1 6-3 in the Chile 2 Masters 4 round of 16 on clay. The result followed the form book — Sergio Cortes came in leading the head-to-head 2–0. Sergio Cortes extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-03-23 | Chile 1 Masters 1 | QF | clay | Sergio Cortes | 6-4 7-5 |
| 1996-03-23 | Chile 1 Masters 3 | R16 | clay | Sergio Cortes | 6-3 6-0 |