Caroline Wozniacki defeated Anett Kontaveit 3-6 7-6 6-2 in the Wimbledon round of 32 on grass. The upset overturned the form book — Anett Kontaveit came in leading the head-to-head 2–1, defending last year's round of 128. Caroline Wozniacki narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2018-10-01 | Beijing | R16 | hard | Caroline Wozniacki | 7-5 6-4 |
| 2018-05-14 | Rome | QF | clay | Anett Kontaveit | 6-3 6-1 |
| 2016-06-06 | Nottingham | R16 | grass | Anett Kontaveit | 6-7(5) 6-3 7-5 |
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 198). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About