Alice Canepa defeated Desislava Topalova 3-6 7-5 6-3 in the Taranto 25K round of 32 on clay. The upset overturned the form book — Desislava Topalova came in leading the head-to-head 1–0. Alice Canepa claimed a first win over Desislava Topalova in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-27 | Oporto 25K | SF | clay | Desislava Topalova | 6-3 7-5 |