Flavia Pennetta defeated Venus Williams 6-4 2-6 6-4 in the Moscow round of 32 on hard. The upset overturned the form book — Venus Williams came in leading the head-to-head 4–3, 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 |
|---|---|---|---|---|---|
| 2014-02-17 | Dubai | QF | hard | Venus Williams | 6-3 7-5 |
| 2009-08-10 | Cincinnati | R16 | hard | Flavia Pennetta | 7-6(2) 6-4 |
| 2009-02-23 | Acapulco | F | hard | Venus Williams | 6-1 6-2 |
| 2008-10-13 | Zurich | F | hard | Venus Williams | 7-6(1) 6-2 |
| 2008-05-26 | Roland Garros | R32 | clay | Flavia Pennetta | 7-5 6-3 |
| 2007-10-08 | Bangkok | SF | hard | Flavia Pennetta | 6-4 7-6(8) |
| 2007-09-24 | Seoul | SF | hard | Venus Williams | 6-2 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 (200 vs 199). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About