Maria Paola Zavagli defeated Alice Canepa 6-3 6-7 6-4 in the Orbetello 25K round of 32 on clay. The upset overturned the form book — Alice Canepa came in leading the head-to-head 1–0, but Maria Paola Zavagli had been the form player, winning 4 of their last 8 on clay. Maria Paola Zavagli claimed a first win over Alice Canepa in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-03-20 | Taranto 25K | R32 | clay | Alice Canepa | 6-4 2-6 7-6(4) |