Marcelo Rebolledo defeated Gonzalo Fernandez 6-4 5-7 6-3 in the Chile Masters 1 round of 16 on clay. The upset overturned the form book — Gonzalo Fernandez came in leading the head-to-head 1–0. Marcelo Rebolledo claimed a first win over Gonzalo Fernandez in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1992-10-05 | Chile Masters 1 | R16 | clay | Gonzalo Fernandez | 6-2 3-6 7-6 |