Iveta Benesova defeated Flavia Pennetta 1-6 6-3 6-4 in the Estoril round of 16 on clay. The result followed the form book — Iveta Benesova came in leading the head-to-head 3–2, defending last year's round of 16. Iveta Benesova extended the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2011-03-21 | Miami | R64 | hard | Iveta Benesova | 6-3 6-0 |
| 2009-08-24 | New Haven | R16 | hard | Flavia Pennetta | 7-6(1) 6-4 |
| 2009-02-23 | Acapulco | SF | hard | Flavia Pennetta | 6-3 6-3 |
| 2008-04-14 | Estoril | R16 | clay | Iveta Benesova | 6-2 6-2 |
| 2004-03-01 | Acapulco | F | hard | Iveta Benesova | 7-6(5) 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 (5 vs 200). ATP, WTA & Challenger.