Diego Cristin defeated Jhonnatan Medina Alvarez 6-4 6-4 in the Chile F4 round of 32 on clay. The upset overturned the form book — Jhonnatan Medina Alvarez came in leading the head-to-head 2–0. Diego Cristin 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 |
|---|---|---|---|---|---|
| 2006-03-06 | Venezuela 1 2 | SF | hard | Jhonnatan Medina Alvarez | 6-4 6-3 |
| 2006-03-06 | Venezuela 1 3 | R16 | hard | Jhonnatan Medina Alvarez | 6-1 5-7 6-4 |