Caroline Wozniacki defeated Maria Sharapova 6-4 2-6 6-2 in the US Open round of 16 on hard. The upset overturned the form book — Maria Sharapova came in leading the head-to-head 7–3, but Caroline Wozniacki had been the form player, winning 4 of their last 6 on hard. Caroline Wozniacki narrowed the head-to-head to 7–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-01-14 | Australian Open | R32 | hard | Maria Sharapova | 6-4 4-6 6-3 |
| 2015-05-04 | Madrid | QF | clay | Maria Sharapova | 6-1 3-6 6-3 |
| 2014-10-20 | WTA Finals | RR | hard | Caroline Wozniacki | 7-6(4) 6-7(5) 6-2 |
| 2013-03-04 | Indian Wells | F | hard | Maria Sharapova | 6-2 6-2 |
| 2012-03-19 | Miami | SF | hard | Maria Sharapova | 4-6 6-2 6-4 |
| 2011-05-09 | Rome | SF | clay | Maria Sharapova | 7-5 6-3 |
| 2011-03-07 | Indian Wells | SF | hard | Caroline Wozniacki | 6-1 6-2 |
| 2010-08-30 | US Open | R16 | hard | Caroline Wozniacki | 6-3 6-4 |
| 2008-05-12 | Rome | R16 | clay | Maria Sharapova | 6-4 7-6(3) |
| 2008-02-18 | Doha | QF | hard | Maria Sharapova | 6-0 6-1 |
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 (199 vs 164). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About