Caroline Wozniacki advanced when Dominika Cibulkova retired 3-6 7-6 3-1 in the Tokyo quarter-final. Caroline Wozniacki extended the head-to-head to 10–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2016-02-08 | St. Petersburg | R16 | hard | Dominika Cibulkova | 6-4 7-5 |
| 2012-10-15 | Moscow | QF | hard | Caroline Wozniacki | 6-2 6-7(1) 6-1 |
| 2012-08-20 | New Haven | QF | hard | Caroline Wozniacki | 6-2 6-1 |
| 2012-01-09 | Sydney | R16 | hard | Caroline Wozniacki | 7-5 2-6 6-4 |
| 2011-06-20 | Wimbledon | R16 | grass | Dominika Cibulkova | 1-6 7-6(5) 7-5 |
| 2011-01-17 | Australian Open | R32 | hard | Caroline Wozniacki | 6-4 6-3 |
| 2011-01-10 | Sydney | R16 | hard | Dominika Cibulkova | 6-3 6-3 |
| 2010-08-30 | US Open | QF | hard | Caroline Wozniacki | 6-2 7-5 |
| 2010-08-23 | New Haven | R16 | hard | Caroline Wozniacki | 6-4 6-1 |
| 2010-02-15 | Dubai | R32 | hard | Caroline Wozniacki | 6-2 7-6(2) |
| 2009-01-12 | Sydney | R32 | hard | Caroline Wozniacki | 6-1 6-2 |
| 2008-08-18 | New Haven | R32 | hard | Caroline Wozniacki | 7-6(7) 0-0 RET |
| 2007-09-17 | Beijing | R32 | hard | Dominika Cibulkova | 6-0 6-7(5) 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 107). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About