The Serb tied Roger Federer for second-most wins for a man in French Open history.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
Citi Open
|
1/32 | Tim Smyczek |
7-6
6-2 |
| 2015 |
BB&T Atlanta Open
|
1/16 | Richard Berankis |
6-4
6-4 |
| 2012 |
US Open, Qualification
|
1/16 | Tim Smyczek |
7-6
5-7 4-6 |
| 2012 |
SAP Open, Qualification
|
Quarter Finals | Tim Smyczek |
3-6
2-4 |
| 2008 |
Humacao
|
Championship | Tim Smyczek |
2-6
7-5 6-3 |
| 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 |
Serbia Open
|
1/16 | Federico Delbonis |
4-6
6-3 1-6 |
| 2021 |
Andalucia Open
|
1/8 | Albert Ramos-Vinolas |
6-3
4-6 6-3 |
| 2021 |
Andalucia Open
|
1/16 | Richard Berankis |
4-6
7-6 5-7 |
| 2021 |
Miami Open
|
1/32 | Jan-Lennard Struff |
6-3
6-4 |
| 2021 |
Miami Open
|
1/64 | Richard Berankis |
6-7
2-6 |
