Alexandre Bonatto defeated Cristian Villagran 6-3 6-1 in the Jamaica F2 round of 32 on hard. The upset overturned the form book — Cristian Villagran came in leading the head-to-head 2–1. Alexandre Bonatto narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-04-26 | Argentina F1 | R32 | clay | Cristian Villagran | 6-3 6-2 |
| 2003-04-28 | Argentina 1 | R32 | clay | Alexandre Bonatto | 6-2 7-5 |
| 2003-04-14 | Chile F2 | R32 | clay | Cristian Villagran | 6-1 6-2 |