The Serb tied Roger Federer for second-most wins for a man in French Open history.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2015 |
Wimbledon
|
1/64 | Richard Berankis |
2-6
2-5 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
Poprad-Tatry
|
1/8 | Mohamed Safwat |
5-7
6-1 4-6 |
| 2018 |
Roland Garros ATP
|
1/64 | Karen Khachanov |
7-6
6-3 6-3 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 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 |
| 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 |
