Flavia Pennetta defeated Iveta Benesova 6-3 6-3 in the Acapulco semi-final on hard. The upset overturned the form book — Iveta Benesova came in leading the head-to-head 4–3, defending last year's quarter-final, but Flavia Pennetta had been the form player, winning 3 of their last 8 on hard. Flavia Pennetta narrowed the head-to-head to 4–4.
| 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 |
| 2008-04-14 | Estoril | R16 | clay | Iveta Benesova | 6-2 6-2 |
| 2005-10-16 | Zurich | Q16 | hard | Flavia Pennetta | 7-5 6-3 |
| 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 |
| 2002-07-01 | Orbetello 50K | QF | clay | Flavia Pennetta | 6-4 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