The Russian is on a roll, but expect the Canadian to give him all he can handle.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Australian Open ATP
|
1/64 | Daniil Medvedev |
2-6
2-6 4-6 |
| 2020 |
Sofia Open
|
Final | Jannik Sinner |
6-4
3-6 7-6 |
| 2020 |
Sofia Open
|
Semi Finals | Vasek Pospisil |
6-7
6-2 6-0 |
| 2020 |
Sofia Open
|
Quarter Finals | Vasek Pospisil |
3-6
2-6 |
| 2020 |
Sofia Open
|
1/8 | Vasek Pospisil |
6-3
6-4 |
| 2020 |
Sofia Open
|
1/16 | Vasek Pospisil |
6-2
5-7 7-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2010 |
Wimbledon
England, Wimbledon |
Championship | David Ferrer |
4-6
2-6 3-6 |
| 2010 |
Gerry Weber Open
Germany, Halle |
Championship | Andreas Beck |
6-2
3-6 7-6 |
| 2010 |
Gerry Weber Open
Germany, Halle |
Championship | Nicolas Kiefer |
4-6
6-1 7-5 |
| 2010 |
Mutua Madrilena Masters Madrid, Qualification
|
Championship | Filippo Volandri |
4-6
2-6 |
