Jana Nejedly defeated Nana Smith 6-2 6-2 in the Santa Clara 75K qualifying round on hard. The upset overturned the form book — Nana Smith came in leading the head-to-head 2–0. Jana Nejedly claimed a first win over Nana Smith in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-25 | Dallas 50K | SF | hard | Nana Smith | 6-7 6-4 6-2 |
| 1999-07-26 | Salt Lake City 50K | QF | hard | Nana Smith | 7-6 3-6 6-4 |