The former No. 1 and potential future No. 1 were playing each other for the first time.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Internazionali BNL d'Italia
|
1/8 | Garbine Muguruza |
6-4
6-1 |
| 2020 |
Internazionali BNL d'Italia
|
1/16 | Johanna Konta |
0-6
4-6 |
| 2020 |
US Open WTA
|
1/32 | Sorana Cirstea |
2-6
7-6 6-4 |
| 2020 |
US Open WTA
|
1/64 | Johanna Konta |
6-7
1-6 |
| 2020 |
Western & Southern Open
|
Semi Finals | Victoria Azarenka |
6-4
4-6 1-6 |
| 2020 |
Western & Southern Open
|
Quarter Finals | Johanna Konta |
6-4
6-3 |
| 2020 |
Western & Southern Open
|
1/8 | Johanna Konta |
6-4
6-2 |
| 2020 |
Western & Southern Open
|
1/16 | Johanna Konta |
6-2
6-0 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Internazionali BNL d'Italia, Qualification
|
1/16 | Marco Cecchinato |
1-6
4-6 |
| 2020 |
Internazionali BNL d'Italia, Qualification
|
1/32 | Bradley Klahn |
2-6
6-4 6-7 |
| 2020 |
Aix en Provence
|
1/16 | Antoine Hoang |
0-6
2-6 |
