Jelena Jankovic defeated Flavia Pennetta 6-2 6-1 in the Tokyo round of 16 on hard. The result followed the form book — Jelena Jankovic came in leading the head-to-head 7–2, defending last year's quarter-final. Jelena Jankovic extended the head-to-head to 8–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2014-05-12 | Rome | R16 | clay | Jelena Jankovic | 6-2 6-3 |
| 2014-04-21 | Stuttgart | R16 | clay | Jelena Jankovic | 3-6 6-2 6-3 |
| 2012-02-20 | Dubai | R16 | hard | Jelena Jankovic | 6-4 6-2 |
| 2009-04-27 | Stuttgart | QF | clay | Flavia Pennetta | 2-6 6-4 6-4 |
| 2008-10-13 | Zurich | R16 | hard | Flavia Pennetta | 5-7 6-3 6-3 |
| 2008-10-06 | Moscow | QF | hard | Jelena Jankovic | 7-6(6) 6-3 |
| 2008-05-12 | Rome | R32 | clay | Jelena Jankovic | 6-1 6-4 |
| 2005-05-02 | Berlin | R32 | grass | Jelena Jankovic | 2-6 6-4 7-6(1) |
| 2004-04-26 | Budapest | SF | clay | Jelena Jankovic | 6-3 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 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About