After taking daughter Olympia to the zoo, Serena edged Osaka in a friendly contest Friday.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Serbia Open
|
1/16 | Filip Krajinovic |
7-5
5-7 6-3 |
| 2021 |
Monte Carlo Masters
|
1/8 | Fabio Fognini |
6-2
7-6 |
| 2021 |
Monte Carlo Masters
|
1/16 | Filip Krajinovic |
6-0
6-3 |
| 2021 |
Monte Carlo Masters
|
1/32 | Filip Krajinovic |
6-1
2-0 |
| 2021 |
Dubai Tennis Championships
|
1/8 | Lloyd Harris |
7-6
6-4 |
| 2021 |
Dubai Tennis Championships
|
1/16 | Filip Krajinovic |
5-7
4-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Belgrade
|
1/8 | Damir Dzumhur |
6-4
6-3 |
| 2021 |
Belgrade
|
1/16 | Philipp Kohlschreiber |
5-7
6-4 2-6 |
| 2020 |
Parma
|
1/8 | Marco Cecchinato |
7-5
6-3 |
| 2020 |
Parma
|
1/16 | Philipp Kohlschreiber |
3-6
1-6 |
| 2020 |
Roland Garros ATP
|
1/64 | Cristian Garin |
6-4
4-6 6-1 6-4 |
