Flavia Pennetta defeated Iveta Benesova 6-4 6-4 in the Orbetello 50K qualifying round on clay. The upset overturned the form book — Iveta Benesova came in leading the head-to-head 4–2. Flavia Pennetta narrowed the head-to-head to 4–3.
| 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 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 |
| 2004-04-12 | Estoril | R16 | clay | Iveta Benesova | 1-6 6-3 6-4 |
| 2004-03-01 | Acapulco | F | hard | Iveta Benesova | 7-6 6-4 |
Averages over each player's completed matches in the selected window (200 vs 5). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About