After taking daughter Olympia to the zoo, Serena edged Osaka in a friendly contest Friday.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Seville
|
1/32 | Inigo Cervantes |
3-6
0-6 |
| 2019 |
Mallorca
|
1/32 | Matteo Viola |
2-6
2-6 |
| 2019 |
Segovia
|
1/32 | Frederico Gil |
6-7
4-6 |
| 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 |
| 2020 |
Rolex Paris Masters
|
1/32 | Feliciano Lopez |
6-7
1-6 |
