After taking daughter Olympia to the zoo, Serena edged Osaka in a friendly contest Friday.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2014 |
bet-at-home Open - German Tennis Championships, Qualification
|
1/6 (Special Qual) | Filip Krajinovic |
3-6
2-6 |
| 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 |
|---|---|---|---|---|
| 2021 |
Delray Beach Open
|
1/16 | Thiago Monteiro |
3-6
5-7 |
| 2020 |
Campinas
|
1/8 | Mohamed Safwat |
6-2
4-6 3-6 |
| 2020 |
Sao Paulo
|
1/8 | Frederico Ferreira Silva |
6-3
6-1 |
| 2020 |
Sao Paulo
|
1/16 | Thomaz Bellucci |
6-2
6-0 |
