| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2014 |
US Open
|
1/64 | Tim Smyczek |
6-4
3-6 2-6 6-7 |
| 2010 |
BNP Paribas Open, Qualification
|
Championship | Tim Smyczek |
6-1
6-0 |
| 2008 |
Bradenton
|
Championship | Tim Smyczek |
4-6
4-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Davis Cup Finals, Final Stage
|
Championship | Andrey Rublev |
1-6
2-6 |
| 2019 |
Davis Cup Finals, Group A
|
Championship | Filip Krajinovic |
5-7
6-7 |
| 2019 |
Davis Cup Finals, Group A
|
Championship | Filip Krajinovic |
6-2
6-4 |
| 2019 |
Swiss Indoors Basel
|
Quarter Finals | Stefanos Tsitsipas |
3-6
6-4 6-4 |
| 2019 |
Swiss Indoors Basel
|
1/8 | Filip Krajinovic |
6-2
6-4 |
| 2019 |
Swiss Indoors Basel
|
1/16 | Filip Krajinovic |
1-6
4-6 |
| 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 |
