Karin Kschwendt defeated Alice Canepa 6-4 6-1 in the Sofia 25K round of 16 on clay. The upset overturned the form book — Alice Canepa came in leading the head-to-head 1–0. Karin Kschwendt claimed a first win over Alice Canepa in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-27 | Oporto 25K | R32 | clay | Alice Canepa | 7-6 6-1 |