Jessica Orselli defeated Natalia Guitler 6-3 6-2 in the Santiago 10K round of 32 on clay. The upset overturned the form book — Natalia Guitler came in leading the head-to-head 1–0. Jessica Orselli claimed a first win over Natalia Guitler in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-10-23 | Luque 10K | R16 | clay | Natalia Guitler | 5-7 6-1 6-1 |