Kaia Kanepi defeated Flavia Pennetta 6-3 6-7 6-2 in the Madrid round of 64 on clay. The result followed the form book — Kaia Kanepi came in defending last year's round of 64. Kaia Kanepi extended the head-to-head to 5–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2014-02-17 | Dubai | R32 | hard | Flavia Pennetta | 7-5 6-4 |
| 2011-09-26 | Tokyo | R64 | hard | Kaia Kanepi | 3-6 6-4 6-4 |
| 2010-07-12 | Palermo | F | clay | Kaia Kanepi | 6-4 6-3 |
| 2008-08-11 | Olympics | R64 | hard | Kaia Kanepi | 6-2 7-6(6) |
| 2008-03-10 | Indian Wells | R64 | hard | Flavia Pennetta | 6-2 6-1 |
| 2008-02-25 | Acapulco | SF | hard | Flavia Pennetta | 6-4 6-2 |
| 2008-02-11 | Vina Del Mar | QF | clay | Flavia Pennetta | 6-3 6-3 |
| 2007-01-15 | Australian Open | R128 | hard | Kaia Kanepi | 7-5 7-6(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 (199 vs 107). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About