Sergio Cortes defeated Juan Garat 6-1 7-6 in the Chile Masters 2 qualifying round on clay. The upset overturned the form book — Juan Garat came in leading the head-to-head 1–0. Sergio Cortes claimed a first win over Juan Garat in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1992-03-16 | Brazil 1 Masters 2 | R32 | clay | Juan Garat | 7-6 6-4 |