Sergio Cortes defeated Jan Gruninger 5-7 6-1 6-3 in the Chile 1 Masters 1 round of 16 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 |
|---|---|---|---|---|---|
| 1996-03-23 | Chile 1 Masters 3 | R32 | clay | Sergio Cortes | 6-3 7-6 |