Gabriel Keymer defeated Marcelo Rebolledo 6-0 4-6 6-4 in the Chile Masters 3 round of 32 on clay. The upset overturned the form book — Marcelo Rebolledo came in leading the head-to-head 1–0. Gabriel Keymer claimed a first win over Marcelo Rebolledo in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-03-23 | Chile 1 Masters 2 | QF | clay | Marcelo Rebolledo | 6-0 6-2 |