Marcelo Rebolledo defeated Juan Robinson Gamonal 6-1 6-3 in the Chile 1 Masters 3 round of 16 on clay. The upset overturned the form book — Juan Robinson Gamonal came in leading the head-to-head 1–0. Marcelo Rebolledo claimed a first win over Juan Robinson Gamonal in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-03-23 | Chile 1 Masters 2 | SF | clay | Juan Robinson Gamonal | 7-5 2-6 6-3 |