Federico Dondo defeated Miguel Miranda 6-3 7-6 in the Chile 2 Masters 2 round of 16 on clay. The upset overturned the form book — Miguel Miranda came in leading the head-to-head 1–0. Federico Dondo claimed a first win over Miguel Miranda in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-08 | Argentina F4 | R32 | clay | Miguel Miranda | 7-5 6-3 |