Gabriel Pitta defeated Jhonnatan Medina Alvarez 7-6 6-3 in the Venezuela 1 4 round of 16 on hard. The upset overturned the form book — Jhonnatan Medina Alvarez came in leading the head-to-head 2–0. Gabriel Pitta claimed a first win over Jhonnatan Medina Alvarez in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-12-04 | Brazil F22 | QF | hard | Jhonnatan Medina Alvarez | 6-2 6-7(5) 7-5 |
| 2006-11-06 | Brazil F18 | R16 | clay | Jhonnatan Medina Alvarez | 6-2 1-6 6-1 |