Jhonnatan Medina Alvarez defeated Antonio Pastorino 7-5 7-6 in the Chile F3 round of 16 on clay. The upset overturned the form book — Antonio Pastorino came in leading the head-to-head 1–0. Jhonnatan Medina Alvarez claimed a first win over Antonio Pastorino in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-09-06 | Argentina F5 | R32 | clay | Antonio Pastorino | 6-1 6-2 |