After taking daughter Olympia to the zoo, Serena edged Osaka in a friendly contest Friday.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2017 |
Rolex Paris Masters
|
Final | Jack Sock |
7-5
4-6 1-6 |
| 2014 |
Savannah
|
Semi Finals | Jack Sock |
6-3
4-6 4-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Cary
|
1/8 | Prajnesh Gunneswaran |
6-7
6-2 7-6 |
| 2020 |
Cary
|
1/16 | Jack Sock |
6-7
3-6 |
| 2020 |
Roland Garros ATP
|
1/32 | Dominic Thiem |
1-6
3-6 6-7 |
| 2020 |
Roland Garros ATP
|
1/64 | Jack Sock |
4-6
4-6 3-6 |
| 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 |
