Caroline Wozniacki defeated Sloane Stephens 7-6 6-2 in the New Haven quarter-final on hard. The result followed the form book — Caroline Wozniacki came in leading the head-to-head 5–1, defending last year's semi-final. Caroline Wozniacki extended the head-to-head to 6–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2017-08-07 | Toronto | SF | hard | Caroline Wozniacki | 6-2 6-3 |
| 2016-01-04 | Auckland | SF | hard | Sloane Stephens | 6-2 7-6(3) |
| 2014-06-16 | Eastbourne | R16 | grass | Caroline Wozniacki | 6-3 6-3 |
| 2014-03-17 | Miami | R32 | hard | Caroline Wozniacki | 6-1 6-0 |
| 2013-09-30 | Beijing | R16 | hard | Caroline Wozniacki | 6-3 6-1 |
| 2011-03-07 | Indian Wells | R64 | hard | Caroline Wozniacki | 6-3 6-2 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.