Olga Barabanschikova defeated Conchita Martinez 2-6 6-2 6-4 in the Sydney round of 32 on hard. The upset overturned the form book — Conchita Martinez came in leading the head-to-head 2–0, defending last year's round of 16. Olga Barabanschikova claimed a first win over Conchita Martinez in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-01-17 | Australian Open | R64 | hard | Conchita Martinez | 6-3 4-6 6-3 |
| 1997-03-31 | Hilton Head | R32 | clay | Conchita Martinez | 6-7 6-4 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.