After taking daughter Olympia to the zoo, Serena edged Osaka in a friendly contest Friday.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2010 |
Wimbledon, Qualification
|
Championship | Robert Kendrick |
6-4
6-2 |
| 2008 |
Knoxville
|
Championship | Filip Krajinovic |
5-7
6-4 6-3 |
| 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 |
|---|---|---|---|---|
| 2013 |
Sacramento
|
1/16 | Thanasi Kokkinakis |
6-7
3-6 |
| 2012 |
Panamacity
|
1/16 | Rogerio Dutra Silva |
3-6
0-3 |
