Klara Koukalova defeated Flavia Pennetta 7-5 6-2 in the New Haven round of 32 on hard. The upset overturned the form book — Flavia Pennetta came in leading the head-to-head 5–3, defending last year's quarter-final. Klara Koukalova narrowed the head-to-head to 5–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2014-08-18 | New Haven | R32 | hard | Flavia Pennetta | 6-1 6-3 |
| 2013-07-08 | Palermo | R32 | clay | Klara Koukalova | 6-2 2-6 6-3 |
| 2011-02-14 | Dubai | R32 | hard | Flavia Pennetta | 5-7 6-1 6-2 |
| 2010-06-21 | Wimbledon | R32 | grass | Klara Koukalova | 6-2 6-3 |
| 2008-02-11 | Vina Del Mar | F | clay | Flavia Pennetta | 6-4 5-4 RET |
| 2005-07-18 | Palermo | SF | clay | Klara Koukalova | 6-4 6-0 |
| 2004-08-09 | Sopot | F | clay | Flavia Pennetta | 7-5 3-6 6-3 |
| 2004-07-19 | Palermo | QF | clay | Flavia Pennetta | 6-4 6-2 |
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 (76 vs 189). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About