Juan Sebastian Vivanco defeated Cristhian Ignacio Benedetti 4-6 6-4 6-3 in the Chile F2 round of 32 on clay. The upset overturned the form book — Cristhian Ignacio Benedetti came in leading the head-to-head 2–0. Juan Sebastian Vivanco claimed a first win over Cristhian Ignacio Benedetti in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-06-21 | Argentina F10 | R32 | clay | Cristhian Ignacio Benedetti | 7-5 6-2 |
| 2008-09-15 | Ecuador F4 | QF | clay | Cristhian Ignacio Benedetti | 6-3 6-2 |