Nicolas Jara Lozano defeated Agustin Picco 6-4 7-5 in the Chile F3 round of 32 on clay. The upset overturned the form book — Agustin Picco came in leading the head-to-head 2–1, but Nicolas Jara Lozano had been the form player, winning 6 of their last 10 on clay. Nicolas Jara Lozano narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-11-23 | Argentina F25 | R32 | clay | Nicolas Jara Lozano | 7-6(4) 7-6(2) |
| 2009-05-04 | Argentina F4 | R16 | clay | Agustin Picco | 7-5 6-2 |
| 2009-04-20 | Argentina F2 | R32 | clay | Agustin Picco | 7-6(5) 6-4 |