Antonio Pastorino defeated Juan Pablo Amado 2-6 6-4 6-2 in the Chile F1A round of 32 on clay. The upset overturned the form book — Juan Pablo Amado came in leading the head-to-head 4–2, but Antonio Pastorino had been the form player, winning 5 of their last 10 on clay. Antonio Pastorino narrowed the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-09-07 | Argentina F14 | R32 | clay | Juan Pablo Amado | 6-4 7-6(1) |
| 2008-07-07 | Argentina F7 | SF | clay | Antonio Pastorino | 7-6(3) 6-4 |
| 2008-06-30 | Argentina F6 | QF | clay | Juan Pablo Amado | 6-4 6-4 |
| 2008-06-23 | Argentina F5 | R16 | clay | Juan Pablo Amado | 6-4 3-6 6-4 |
| 2007-06-18 | Argentina F9 | R32 | clay | Juan Pablo Amado | 6-3 1-6 7-6(3) |
| 2006-03-13 | Argentina F1 | R32 | clay | Antonio Pastorino | 6-1 6-0 |