Iveta Benesova defeated Anna Chakvetadze 6-2 6-4 in the Luxembourg round of 16 on hard. The upset overturned the form book — Anna Chakvetadze came in leading the head-to-head 4–0, defending last year's quarter-final. Iveta Benesova claimed a first win over Anna Chakvetadze in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-09-22 | Beijing | R32 | hard | Anna Chakvetadze | 6-4 7-5 |
| 2006-05-08 | Berlin | R64 | grass | Anna Chakvetadze | 6-1 6-3 |
| 2005-08-08 | Los Angeles | R32 | hard | Anna Chakvetadze | 7-5 4-6 6-4 |
| 2005-08-01 | San Diego | R32 | hard | Anna Chakvetadze | 6-4 6-3 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (5 vs 128). ATP, WTA & Challenger.