Diego Del Rio defeated Gabriel Keymer 6-0 6-2 in the Santiago qualifying round of 16 on clay. The upset overturned the form book — Gabriel Keymer came in leading the head-to-head 1–0, but Diego Del Rio had been the form player, winning 3 of their last 10 on clay. Diego Del Rio claimed a first win over Gabriel Keymer in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-05-03 | Chile 1 Masters 2 | R32 | clay | Gabriel Keymer | 3-6 7-6 6-3 |