The Russian is on a roll, but expect the Canadian to give him all he can handle.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2017 |
Delray Beach Open, Qualification
|
Quarter Finals | Tim Smyczek |
2-6
2-6 |
| 2011 |
Honolulu
|
Championship | Vasek Pospisil |
6-1
6-2 |
| 2010 |
Tulsa
|
Championship | Tim Smyczek |
6-2
6-1 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Citi Open
|
1/16 | Milos Raonic |
6-1
6-4 |
| 2019 |
Citi Open
|
1/32 | Tim Smyczek |
4-6
4-6 |
| 2019 |
Citi Open, Qualification
|
1/6 (Special Qual) | Tim Smyczek |
6-7
7-5 3-6 |
| 2019 |
Citi Open, Qualification
|
1/12 (Special Qual) | Tim Smyczek |
6-4
6-2 |
| 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 |
