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 |
|---|---|---|---|---|
| 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 |
| 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 |
