Francesca Lubiani defeated Samantha Smith 7-6 6-0 in the Midland 25K round of 32 on hard. The upset overturned the form book — Samantha Smith came in leading the head-to-head 1–0. Francesca Lubiani claimed a first win over Samantha Smith in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-08 | Rockford 25K | SF | hard | Samantha Smith | 6-4 6-2 |