Germana Di Natale defeated Daniela Olivera 6-2 7-5 in the Lenzerheide 25K qualifying round on clay. The upset overturned the form book — Daniela Olivera came in leading the head-to-head 1–0, but Germana Di Natale had been the form player, winning 3 of their last 6 on clay. Germana Di Natale claimed a first win over Daniela Olivera in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-12-04 | Santa Fe De Bogota | R32 | clay | Daniela Olivera | 5-7 6-1 7-5 |