Anett Kontaveit advanced when Angelique Kerber retired 6-0 2-0 in the Stuttgart round of 16. Anett Kontaveit extended the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2022-04-18 | Stuttgart | R32 | clay | Anett Kontaveit | 3-6 6-4 6-4 |
| 2021-03-01 | Doha | R16 | hard | Anett Kontaveit | 6-1 6-4 |
| 2019-08-12 | Cincinnati | R64 | hard | Anett Kontaveit | 7-6(7) 6-2 |
| 2019-02-11 | Doha | R16 | hard | Angelique Kerber | 6-1 7-6(3) |
| 2017-05-15 | Rome | R32 | clay | Anett Kontaveit | 6-4 6-0 |
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 (198 vs 198). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About