Ruben Gajardo defeated Rodolfo Ramos Paganini 2-6 6-2 6-0 in the Chile Masters 4 round of 32 on clay. The upset overturned the form book — Rodolfo Ramos Paganini came in leading the head-to-head 1–0. Ruben Gajardo claimed a first win over Rodolfo Ramos Paganini in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1991-07-15 | Brazil 5 Masters 3 | R16 | clay | Rodolfo Ramos Paganini | 7-6 6-7 7-6 |