Flavia Pennetta defeated Maria Sharapova 6-3 3-6 6-4 in the US Open round of 32 on hard. The upset overturned the form book — Maria Sharapova came in leading the head-to-head 3–2, defending last year's round of 16, but Flavia Pennetta had been the form player, winning 2 of their last 7 on hard. Flavia Pennetta narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2015-10-25 | WTA Finals | RR | hard | Maria Sharapova | 7-5 6-1 |
| 2015-03-09 | Indian Wells | R16 | hard | Flavia Pennetta | 3-6 6-3 6-2 |
| 2009-08-03 | Los Angeles | SF | hard | Flavia Pennetta | 6-2 4-6 6-3 |
| 2006-06-26 | Wimbledon | R16 | grass | Maria Sharapova | 7-6(5) 3-6 6-3 |
| 2004-03-10 | Indian Wells | R64 | hard | Maria Sharapova | 6-3 4-6 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 (188 vs 198). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About