Natalia Cheng defeated Natasha Lotuffo 6-4 4-6 6-0 in the Santos 10K round of 16 on clay. The upset overturned the form book — Natasha Lotuffo came in leading the head-to-head 2–0, but Natalia Cheng had been the form player, winning 4 of their last 7 on clay. Natalia Cheng claimed a first win over Natasha Lotuffo in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-08-16 | Itaparica 10K | R32 | hard | Natasha Lotuffo | 7-5 6-2 |
| 2008-11-10 | Santiago 10K | R32 | clay | Natasha Lotuffo | 5-7 6-3 6-2 |