Julie Halard Decugis defeated Cara Black 3-6 7-5 7-5 in the Hobart quarter-final on hard. The result followed the form book — Julie Halard Decugis came in leading the head-to-head 2–1, defending last year's round of 16. Julie Halard Decugis extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-30 | US Open | R128 | hard | Julie Halard Decugis | 6-3 5-7 6-3 |
| 1999-06-07 | Birmingham | SF | grass | Julie Halard Decugis | 6-4 6-4 |
| 1999-02-02 | Tokyo | R32 | hard | Cara Black | 6-2 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.