Gonzalo Fernandez defeated Marcelo Rebolledo 6-2 3-6 7-6 in the Chile Masters 1 round of 16 on clay. The upset overturned the form book — Marcelo Rebolledo came in leading the head-to-head 1–0. Gonzalo Fernandez claimed a first win over Marcelo Rebolledo in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1995-09-30 | Chile Masters 1 | R16 | clay | Marcelo Rebolledo | 6-4 5-7 6-3 |