Lubomira Bacheva defeated Olga Barabanschikova 7-6 0-6 6-4 in the Sofia 25K qualifying round on clay. The upset overturned the form book — Olga Barabanschikova came in leading the head-to-head 2–0. Lubomira Bacheva claimed a first win over Olga Barabanschikova in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-18 | Bratislava | R16 | hard | Olga Barabanschikova | 7-5 6-4 |
| 1999-08-02 | Knokke-Heist | R32 | clay | Olga Barabanschikova | 7-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.