Caroline Wozniacki defeated Elena Dementieva 1-6 6-3 7-6 in the New Haven semi-final on hard. The result followed the form book — Caroline Wozniacki came in leading the head-to-head 4–3, defending the title. Caroline Wozniacki extended the head-to-head to 5–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-10-25 | WTA Championships | RR | hard | Caroline Wozniacki | 6-1 6-1 |
| 2010-09-27 | Tokyo | F | hard | Caroline Wozniacki | 1-6 6-2 6-3 |
| 2009-08-10 | Cincinnati | QF | hard | Elena Dementieva | 6-2 6-1 |
| 2009-04-13 | Charleston | SF | clay | Caroline Wozniacki | 6-4 5-7 7-5 |
| 2009-03-23 | Miami | R16 | hard | Caroline Wozniacki | 7-5 6-4 |
| 2008-10-20 | Luxembourg | F | hard | Elena Dementieva | 2-6 6-4 7-6(4) |
| 2008-08-11 | Olympics | R16 | hard | Elena Dementieva | 7-6(3) 6-2 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.