The Serb tied Roger Federer for second-most wins for a man in French Open history.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2016 |
US Open
United States, New York, Flushing Meadows |
1/64 | Richard Berankis |
3-6
7-6 6-4 6-2 |
| 2016 |
Gerry Weber Open
Germany, Halle |
1/16 | Malek Jaziri |
5-7
4-6 |
| 2015 |
Kremlin Cup By Bank Of Moscow
|
1/16 | Richard Berankis |
4-6
4-6 |
| 2014 |
Campell's Hall of Fame Tennis Championships
|
1/16 | Malek Jaziri |
5-7
3-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Singapore Open, Qualification
|
Quarter Finals | John-Patrick Smith |
5-7
6-7 |
| 2021 |
Biella
|
1/16 | Dmitry Popko |
6-1
6-3 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Australian Open ATP
|
1/32 | Karen Khachanov |
6-2
6-4 6-4 |
| 2021 |
Australian Open ATP
|
1/64 | Richard Berankis |
6-2
7-5 6-3 |
| 2021 |
Murray River Open
|
1/8 | Jiri Vesely |
6-4
6-2 |
| 2021 |
Murray River Open
|
1/16 | Richard Berankis |
7-6
7-5 |
| 2021 |
Murray River Open
|
1/32 | Richard Berankis |
2-6
2-6 |
