Cristian Villagran defeated Juan Pablo Amado 4-6 6-3 6-3 in the Uruguay F1 round of 16 on clay. The result followed the form book — Cristian Villagran came in leading the head-to-head 3–2. Cristian Villagran extended the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-04-30 | Argentina F2 | R16 | clay | Cristian Villagran | 6-1 7-5 |
| 2006-05-29 | Argentina F9 | R16 | clay | Cristian Villagran | 6-4 7-6(7) |
| 2006-05-15 | Argentina F7 | R16 | clay | Juan Pablo Amado | 6-3 6-3 |
| 2006-04-17 | Uruguay F2 | R16 | clay | Cristian Villagran | 6-4 3-6 6-4 |
| 2005-09-12 | Argentina F11 | R32 | clay | Juan Pablo Amado | 4-1 |