Jelena Jankovic advanced when Anna Chakvetadze retired 6-1 0-0 in the Dubai quarter-final. Jelena Jankovic narrowed the head-to-head to 7–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-15 | Eastbourne | R32 | grass | Anna Chakvetadze | 6-7(5) 6-3 6-2 |
| 2007-11-05 | WTA Tour Championships | RR | carpet | Anna Chakvetadze | 6-4 0-6 6-3 |
| 2007-06-18 | 's-Hertogenbosch | F | grass | Anna Chakvetadze | 7-6(2) 3-6 6-3 |
| 2007-04-30 | Warsaw | QF | clay | Jelena Jankovic | 7-6(1) 3-1 RET |
| 2006-09-25 | Guangzhou | SF | hard | Anna Chakvetadze | 7-5 2-0 RET |
| 2006-05-01 | Warsaw | R32 | clay | Anna Chakvetadze | 7-5 6-3 |
| 2005-08-22 | New Haven | R32 | hard | Anna Chakvetadze | 6-3 3-6 6-2 |
| 2005-06-20 | Wimbledon | R128 | grass | Jelena Jankovic | 6-4 6-2 |
| 2005-03-09 | Indian Wells | R64 | hard | Anna Chakvetadze | 2-6 6-2 6-4 |
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 (200 vs 127). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About