The former No. 1 and potential future No. 1 were playing each other for the first time.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Madrid Open
|
1/16 | Alexander Zverev |
4-6
1-6 |
| 2019 |
Madrid Open
|
1/32 | David Ferrer |
6-4
4-6 6-4 |
| 2019 |
Barcelona Open
|
1/8 | Rafael Nadal |
6-3
6-3 |
| 2019 |
Barcelona Open
|
1/16 | David Ferrer |
6-3
6-1 |
| 2019 |
Barcelona Open
|
1/32 | David Ferrer |
6-3
6-1 |
| 2019 |
Miami Open
|
1/16 | Frances Tiafoe |
5-7
6-3 6-3 |
| 2019 |
Miami Open
|
1/32 | David Ferrer |
2-6
7-5 6-3 |
| 2019 |
Miami Open
|
1/64 | David Ferrer |
3-6
2-6 |
| 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 |
