Keys will return to the court for the first time since the French Open last September.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
St. Petersburg Open
|
1/8 | Roberto Bautista Agut |
6-7
6-3 3-6 |
| 2018 |
St. Petersburg Open
|
1/16 | Mikhail Youzhny |
6-7
4-6 |
| 2018 |
US Open ATP
|
1/64 | Marcos Baghdatis |
6-4
6-4 2-6 3-1 |
| 2018 |
Rogers Cup
|
1/16 | Robin Haase |
5-7
2-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Qatar Total Open
|
1/16 | Madison Keys |
6-4
6-1 |
| 2020 |
Roland Garros WTA
|
1/64 | Zhang Shuai |
6-3
7-6 |
| 2020 |
US Open WTA
|
1/16 | Alize Cornet |
6-7
2-3 |
| 2020 |
US Open WTA
|
1/32 | Madison Keys |
6-2
6-1 |
| 2020 |
US Open WTA
|
1/64 | Madison Keys |
6-1
6-1 |
