Osaka's quest for major No. 4 begins with a brutal opening round against Pavlyuchenkova.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Wimbledon ATP
|
1/32 | Matteo Berrettini |
6-1
7-6 6-3 |
| 2019 |
Wimbledon ATP
|
1/64 | Marcos Baghdatis |
2-6
4-6 4-6 |
| 2019 |
Busan
|
1/16 | Marcos Baghdatis |
6-4
2-6 2-6 |
| 2019 |
Seoul
|
1/16 | Zhe Li |
4-6
2-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Qatar Total Open
|
1/8 | Petra Kvitova |
1-6
3-6 |
| 2021 |
Qatar Total Open
|
1/16 | Anastasia Pavlyuchenkova |
2-6
3-6 |
| 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 |
