Oxana Lyubtsova defeated Elena Chalova 6-0 4-6 6-0 in the Kiev 10K qualifying round on clay. The upset overturned the form book — Elena Chalova came in leading the head-to-head 2–0. Oxana Lyubtsova claimed a first win over Elena Chalova in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-11-02 | Ismaning 50K | R32 | carpet | Elena Chalova | 6-2 2-6 6-4 |
| 2009-09-28 | Helsinki 25K | R16 | hard | Elena Chalova | 6-4 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.