Ruben Gajardo defeated Diego Del Rio 3-6 6-2 6-4 in the Chile 1 Masters 1 round of 16 on clay. The result followed the form book — Ruben Gajardo came in leading the head-to-head 1–0. Ruben Gajardo extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1991-09-02 | Brazil 6 Masters 2 | R16 | clay | Ruben Gajardo | 6-7 6-3 6-2 |