Paula Catalina Robles Garcia defeated Natalia Cheng 6-1 6-2 in the Sao Paolo 10K round of 16 on clay. The upset overturned the form book — Natalia Cheng came in leading the head-to-head 1–0. Paula Catalina Robles Garcia claimed a first win over Natalia Cheng in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-07-13 | Bogota 25K | R32 | clay | Natalia Cheng | 7-6(4) 6-4 |