After taking daughter Olympia to the zoo, Serena edged Osaka in a friendly contest Friday.
| 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 |
Roland Garros, Qualification WTA
|
1/24 (Special Qual) | Varvara Lepchenko |
1-6
1-6 |
| 2016 |
Roland Garros, Qualification WTA
|
1/48 (Special Qual) | Veronica Cepede Royg |
6-7
7-5 6-4 |
| 2016 |
Istanbul Cup, Qualification
|
1/12 (Special Qual) | Reka-Luca Jani |
3-6
1-6 |
