Marcelo Rebolledo defeated Ruben Gajardo 6-1 7-5 in the Chile 1 Masters 2 round of 32 on clay. Marcelo Rebolledo extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-03-23 | Chile 1 Masters 1 | R16 | clay | Ruben Gajardo | 6-2 6-4 |
| 1992-10-05 | Chile Masters 3 | QF | clay | Marcelo Rebolledo | 6-1 6-3 |