Germana Di Natale defeated Maria Paola Zavagli 7-5 6-2 in the San Severo 10K round of 16 on clay. The upset overturned the form book — Maria Paola Zavagli came in leading the head-to-head 1–0. Germana Di Natale claimed a first win over Maria Paola Zavagli in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-15 | Rome | Q32 | clay | Maria Paola Zavagli | 6-7(2) 6-4 6-4 |