| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2014 |
US Open
|
1/64 | Nick Kyrgios |
5-7
6-7 6-2 6-7 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
St. Petersburg Open
|
1/8 | Roberto Bautista Agut |
6-7
6-3 3-6 |
| 2018 |
St. Petersburg Open
|
1/16 | Mikhail Youzhny |
6-7
4-6 |
| 2018 |
US Open ATP
|
1/64 | Marcos Baghdatis |
6-4
6-4 2-6 3-1 |
| 2018 |
Rogers Cup
|
1/16 | Robin Haase |
5-7
2-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Zhuhai Championships
|
1/16 | Andreas Seppi |
6-7
1-6 |
| 2019 |
Laver Cup
|
Championship | Roger Federer |
6-7
7-5 10-7 |
| 2019 |
US Open ATP
|
1/16 | Andrey Rublev |
7-6
7-6 6-3 |
| 2019 |
US Open ATP
|
1/32 | Nick Kyrgios |
4-6
2-6 4-6 |
| 2019 |
US Open ATP
|
1/64 | Nick Kyrgios |
3-6
6-7 4-6 |
