After taking daughter Olympia to the zoo, Serena edged Osaka in a friendly contest Friday.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2010 |
Kosice
|
Championship | Ruben Ramirez Hidalgo |
6-3
6-2 |
| 2009 |
San Sebastian
|
Championship | Filip Krajinovic |
1-6
5-7 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Australian Open ATP
|
1/16 | Daniil Medvedev |
3-6
3-6 6-4 6-3 0-6 |
| 2021 |
Australian Open ATP
|
1/32 | Filip Krajinovic |
6-2
5-7 6-1 6-4 |
| 2021 |
Australian Open ATP
|
1/64 | Filip Krajinovic |
7-6
6-3 4-6 6-2 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Blois
|
1/32 | Juan Pablo Varillas |
6-3
6-1 |
| 2017 |
Alphen
|
1/16 | Kamil Majchrzak |
3-6
2-6 |
