Karina Habsudova defeated Conchita Martinez 1-6 6-0 6-4 in the Olympics round of 32 on hard. The upset overturned the form book — Conchita Martinez came in leading the head-to-head 3–0. Karina Habsudova claimed a first win over Conchita Martinez in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-12 | Sopot | F | clay | Conchita Martinez | 6-1 6-1 |
| 1998-07-13 | Warsaw | QF | clay | Conchita Martinez | 6-2 6-4 |
| 1997-06-23 | Wimbledon | R128 | grass | Conchita Martinez | 6-1 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.