Simona Halep defeated Angelique Kerber 6-3 5-7 6-4 in the Toronto round of 16 on hard. The upset overturned the form book — Angelique Kerber came in leading the head-to-head 6–4. Simona Halep narrowed the head-to-head to 6–5.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2021-05-10 | Rome | R32 | clay | Angelique Kerber | 1-6 3-3 RET |
| 2019-06-24 | Eastbourne | QF | grass | Angelique Kerber | 6-4 6-3 |
| 2018-05-28 | Roland Garros | QF | clay | Simona Halep | 6-7(2) 6-3 6-2 |
| 2018-01-15 | Australian Open | SF | hard | Simona Halep | 6-3 4-6 9-7 |
| 2016-10-24 | Singapore | RR | hard | Angelique Kerber | 6-4 6-2 |
| 2016-08-15 | Cincinnati | SF | hard | Angelique Kerber | 6-3 6-4 |
| 2016-07-25 | Montreal | SF | hard | Simona Halep | 6-0 3-6 6-2 |
| 2016-06-27 | Wimbledon | QF | grass | Angelique Kerber | 7-5 7-6(2) |
| 2016-04-16 | Fed Cup WG R1: GER vs ROU | RR | clay | Angelique Kerber | 6-2 6-2 |
| 2014-02-10 | Doha | F | hard | Simona Halep | 6-2 6-3 |
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.