Sergio Cortes defeated Marcelo Rebolledo 6-2 6-2 in the Chile 2 Masters 3 semi-final 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 |
|---|---|---|---|---|---|
| 1997-11-08 | Chile 2 Masters 3 | R16 | clay | Sergio Cortes | 6-2 |
| 1992-03-16 | Brazil 1 Masters 4 | R16 | clay | Sergio Cortes | 6-4 6-0 |