The stage was set for a historic moment; the match happened in the second round.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Wimbledon, Qualification ATP
|
1/32 | Daniel Brands |
7-6
6-7 5-7 |
| 2019 |
Libema Open, Qualification
|
Quarter Finals | Tommy Paul |
5-7
4-6 |
| 2019 |
Libema Open, Qualification
|
1/8 | Daniel Brands |
4-6
2-6 |
| 2019 |
Surbiton
|
1/16 | Feliciano Lopez |
5-7
6-3 6-4 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Roland Garros WTA
|
1/32 | Tsvetana Pironkova | |
| 2020 |
Roland Garros WTA
|
1/64 | Serena Williams |
6-7
0-6 |
| 2020 |
US Open WTA
|
Semi Finals | Victoria Azarenka |
6-1
3-6 3-6 |
| 2020 |
US Open WTA
|
Quarter Finals | Serena Williams |
6-4
3-6 2-6 |
| 2020 |
US Open WTA
|
1/8 | Serena Williams |
3-6
7-6 3-6 |
| 2020 |
US Open WTA
|
1/16 | Serena Williams |
6-2
2-6 2-6 |
| 2020 |
US Open WTA
|
1/32 | Serena Williams |
2-6
4-6 |
| 2020 |
US Open WTA
|
1/64 | Serena Williams |
5-7
3-6 |
| 2020 |
Western & Southern Open
|
1/8 | Maria Sakkari |
5-7
7-6 6-1 |
| 2020 |
Western & Southern Open
|
1/16 | Serena Williams |
6-7
6-3 6-7 |
