After taking daughter Olympia to the zoo, Serena edged Osaka in a friendly contest Friday.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2015 |
Szczecin
|
Quarter Finals | Nicolas Almagro |
5-7
1-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
Szczecin
|
1/16 | Facundo Arguello |
7-5
2-1 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Dubai Tennis Championships
|
1/8 | Lloyd Harris |
7-6
6-4 |
| 2021 |
Dubai Tennis Championships
|
1/16 | Filip Krajinovic |
5-7
4-6 |
| 2021 |
Qatar Open
|
1/16 | David Goffin |
6-4
6-4 |
