After taking daughter Olympia to the zoo, Serena edged Osaka in a friendly contest Friday.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2017 |
Biella
|
Semi Finals | Filip Krajinovic |
6-4
7-6 |
| 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 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
San Luis Potosi
|
1/16 | Joao Souza |
6-3
6-4 |
| 2019 |
Santiago
|
1/16 | Facundo Arguello |
6-4
3-6 4-6 |
| 2019 |
Santiago
|
1/32 | Joao Souza |
6-1
6-3 |
| 2019 |
Brasil Open, Qualification
|
1/8 | Alessandro Giannessi |
7-6
6-3 |
