Osaka's quest for major No. 4 begins with a brutal opening round against Pavlyuchenkova.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
US Open WTA
|
1/64 | Anastasia Pavlyuchenkova |
1-6
6-7 |
| 2016 |
Monterrey Open
|
1/16 | Pauline Parmentier |
6-2
6-2 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Roland Garros WTA
|
1/64 | Veronika Kudermetova |
2-6
3-6 |
| 2020 |
Internationaux de Strasbourg
|
1/16 | Magda Linette |
6-4
6-3 |
| 2020 |
Lyon Open
|
1/16 | Daria Kasatkina |
6-2
5-7 6-4 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Phillip Island Trophy
|
1/8 | Daria Kasatkina |
2-6
6-1 6-4 |
| 2021 |
Phillip Island Trophy
|
1/16 | Anastasia Pavlyuchenkova |
7-5
4-6 2-6 |
| 2021 |
Australian Open WTA
|
1/64 | Naomi Osaka |
1-6
2-6 |
| 2021 |
Yarra Valley Classic
|
1/8 | Garbine Muguruza |
6-1
6-2 |
| 2021 |
Yarra Valley Classic
|
1/16 | Anastasia Pavlyuchenkova |
0-6
3-6 |
| 2021 |
Yarra Valley Classic
|
1/32 | Anastasia Pavlyuchenkova |
1-6
4-6 |
