Maria Sharapova defeated Flavia Pennetta 7-5 6-1 in the Singapore round robin on hard. The result followed the form book — Maria Sharapova came in defending last year's round-robin. Maria Sharapova extended the head-to-head to 4–3.
| 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 |
| 2011-08-29 | US Open | R32 | hard | Flavia Pennetta | 6-3 3-6 6-4 |
| 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 3-6 6-3 |
| 2004-03-10 | Indian Wells | R64 | hard | Maria Sharapova | 6-3 4-6 6-4 |
Averages over each player's completed matches in the selected window (114 vs 32). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About