Ekaterina Sysoeva defeated Olga Glouschenko 6-4 6-7 7-5 in the Sochi 25K qualifying round on hard. The upset overturned the form book — Olga Glouschenko came in leading the head-to-head 1–0. Ekaterina Sysoeva claimed a first win over Olga Glouschenko in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-27 | Tbilisi 25K | R16 | clay | Olga Glouschenko | 6-4 2-6 6-4 |