Marcelo Rebolledo defeated Gabriel Keymer 6-0 6-2 in the Chile 1 Masters 2 qualifying round on clay. The upset overturned the form book — Gabriel Keymer came in leading the head-to-head 1–0, but Marcelo Rebolledo had been the form player, winning 4 of their last 10 on clay. Marcelo Rebolledo claimed a first win over Gabriel Keymer in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1995-09-30 | Chile Masters 3 | R32 | clay | Gabriel Keymer | 6-0 4-6 6-4 |