After taking daughter Olympia to the zoo, Serena edged Osaka in a friendly contest Friday.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2010 |
Arad
|
Championship | Filip Krajinovic |
6-2
5-7 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 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2011 |
Blumenau
|
Championship | Diego Junqueira |
2-6
3-6 |
| 2011 |
Blumenau
|
Championship | Martin Vassallo Arguello |
6-0
7-5 |
| 2011 |
Pereira
|
Championship | Eduardo Struvay |
6-1
6-7 4-6 |
| 2011 |
Barranquilla
|
Championship | Flavio Cipolla |
7-6
4-6 3-6 |
| 2011 |
Barranquilla
|
Championship | Martin Vassallo Arguello |
1-6
6-7 |
