After taking daughter Olympia to the zoo, Serena edged Osaka in a friendly contest Friday.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2014 |
US Open
|
1/64 | Tim Smyczek |
6-4
3-6 2-6 6-7 |
| 2010 |
BNP Paribas Open, Qualification
|
Championship | Tim Smyczek |
6-1
6-0 |
| 2008 |
Bradenton
|
Championship | Tim Smyczek |
4-6
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 |
|---|---|---|---|---|
| 2019 |
Citi Open
|
1/16 | Milos Raonic |
6-1
6-4 |
| 2019 |
Citi Open
|
1/32 | Tim Smyczek |
4-6
4-6 |
| 2019 |
Citi Open, Qualification
|
1/6 (Special Qual) | Tim Smyczek |
6-7
7-5 3-6 |
| 2019 |
Citi Open, Qualification
|
1/12 (Special Qual) | Tim Smyczek |
6-4
6-2 |
