
Anastasia Pavlyuchenkova defeated Anett Kontaveit 6-4 6-4 in the Indian Wells round of 64 on hard. The upset overturned the form book — Anett Kontaveit came in leading the head-to-head 4–1. Anastasia Pavlyuchenkova narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2020-02-17 | Dubai | R16 | hard | Anett Kontaveit | 7-6(5) 7-5 |
| 2020-01-13 | Adelaide | R32 | hard | Anastasia Pavlyuchenkova | 6-2 6-4 |
| 2019-04-22 | Stuttgart | R16 | clay | Anett Kontaveit | 6-3 6-2 |
| 2018-04-23 | Stuttgart | QF | clay | Anett Kontaveit | 7-5 6-7(6) 6-4 |
| 2015-08-31 | US Open | R64 | hard | Anett Kontaveit | 7-5 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.