The Russian is on a roll, but expect the Canadian to give him all he can handle.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2015 |
Mutua Madrid Open, Qualification
|
1/14 (Special Qual) | Janko Tipsarevic |
2-6
4-6 |
| 2013 |
Davis Cup Semi final
|
Championship | Janko Tipsarevic |
7-6
6-2 7-6 |
| year | Event | RND | Winner | Results |
|---|
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Australian Open ATP
|
1/64 | Daniil Medvedev |
2-6
2-6 4-6 |
