After taking daughter Olympia to the zoo, Serena edged Osaka in a friendly contest Friday.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2016 |
European Open
Belgium, Antwerp |
1/16 | Inigo Cervantes |
6-1
3-6 6-1 |
| 2016 |
European Open, Qualification
|
Quarter Finals | Michael Berrer |
6-7
4-6 |
| 2016 |
Shanghai Masters, Qualification
|
1/7 (Special Qual) | Mikhail Youzhny |
6-2
6-2 |
| 2016 |
Shanghai Masters, Qualification
|
1/14 (Special Qual) | Michael Berrer |
6-3
6-4 |
| 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 |
