Antonio Pastorino defeated Emiliano Redondi 6-3 6-4 in the Chile 1 1 qualifying round on clay. The upset overturned the form book — Emiliano Redondi came in leading the head-to-head 3–2. Antonio Pastorino narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-02-06 | Panama F1 | SF | clay | Antonio Pastorino | 7-6(4) 2-6 7-5 |
| 2005-09-12 | Uruguay F1 | QF | clay | Emiliano Redondi | 6-3 6-4 |
| 2004-11-22 | Argentina F7 | QF | clay | Emiliano Redondi | 6-2 6-4 |
| 2004-04-26 | Argentina F1 | R32 | clay | Antonio Pastorino | 6-4 6-4 |
| 1999-07-31 | Argentina 2 Masters 1 | R32 | clay | Emiliano Redondi | 6-1 6-1 |