Gabriel Keymer defeated Diego Del Rio 3-6 7-6 6-3 in the Chile 1 Masters 2 round of 32 on clay. The upset overturned the form book — Diego Del Rio came in leading the head-to-head 1–0. Gabriel Keymer claimed a first win over Diego Del Rio in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-02-28 | Santiago | Q16 | clay | Diego Del Rio | 6-0 6-2 |