Ekaterina Ivanova defeated Olga Boulytcheva 2-6 6-0 6-3 in the Charlottesville VA 50K round of 32 on clay. The upset overturned the form book — Olga Boulytcheva came in leading the head-to-head 1–0. Ekaterina Ivanova claimed a first win over Olga Boulytcheva in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-02-16 | Surprise AZ 25K | R16 | hard | Olga Boulytcheva | 6-3 6-3 |