The German won 6-4, 6-2 over the two-time Grand Slam finalist.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
VTB Kremlin Cup
|
1/16 | Mikhail Kukushkin |
4-6
3-6 |
| 2019 |
Nur-Sultan 2
|
Quarter Finals | Ruben Bemelmans |
6-1
3-6 6-3 |
| 2019 |
Nur-Sultan 2
|
1/16 | Evgeny Donskoy |
6-7
6-4 6-7 |
| 2019 |
Orleans
|
1/8 | Mikael Ymer |
3-6
2-6 |
| 2019 |
Orleans
|
1/16 | Evgeny Donskoy |
7-6
6-4 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Karlsruhe
|
1/16 | Jasmine Paolini |
6-3
4-6 1-6 |
| 2019 |
Wimbledon, Qualification WTA
|
1/16 | Lesley Kerkhove |
0-6
6-4 6-4 |
| 2019 |
Wimbledon, Qualification WTA
|
1/32 | Sabine Lisicki |
1-6
6-7 |
| 2019 |
Wimbledon, Qualification WTA
|
1/64 | Sabine Lisicki |
6-3
3-6 6-3 |
| 2019 |
Mallorca Open, Qualification
|
1/6 (Special Qual) | Kaja Juvan |
7-5
4-6 4-6 |
| 2019 |
Mallorca Open, Qualification
|
1/12 (Special Qual) | Sabine Lisicki |
2-6
7-6 2-6 |
