Juan Robinson Gamonal defeated Marcelo Rebolledo 7-5 2-6 6-3 in the Chile 1 Masters 2 semi-final on clay. The upset overturned the form book — Marcelo Rebolledo came in leading the head-to-head 1–0. Juan Robinson Gamonal claimed a first win over Marcelo Rebolledo in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-03-23 | Chile 1 Masters 3 | R16 | clay | Marcelo Rebolledo | 6-1 6-3 |