Katia Piccolini defeated Ekaterina Sysoeva 2-6 6-3 6-0 in the Milan 10K round of 32 on carpet. The upset overturned the form book — Ekaterina Sysoeva came in leading the head-to-head 1–0. Katia Piccolini claimed a first win over Ekaterina Sysoeva in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-17 | Pesaro 10K | QF | clay | Ekaterina Sysoeva | 6-4 6-0 |