Alicia Molik defeated Annabel Ellwood 6-0 6-3 in the Fukuoka 50K semi-final on grass. The upset overturned the form book — Annabel Ellwood came in leading the head-to-head 2–1. Alicia Molik narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-18 | Gold Coast 25K | F | hard | Alicia Molik | 6-4 6-3 |
| 1999-04-05 | Fresno 25K | F | hard | Annabel Ellwood | 3-6 6-4 6-2 |
| 1999-03-29 | Claremont 25K | R16 | hard | Annabel Ellwood | 7-6 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.