Cara Black defeated Julie Halard Decugis 6-2 6-1 in the Tokyo round of 32 on hard. The upset overturned the form book — Julie Halard Decugis came in leading the head-to-head 3–0, defending last year's quarter-final. Cara Black claimed a first win over Julie Halard Decugis in four meetings, narrowing 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 |
| 1999-01-11 | Hobart | QF | hard | Julie Halard Decugis | 3-6 7-5 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.