The Serb tied Roger Federer for second-most wins for a man in French Open history.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2015 |
Open BancSabadell
|
1/32 | Albert Montanes |
6-1
4-6 5-7 |
| 2013 |
Open BancSabadell
|
1/32 | Albert Montanes |
4-6
3-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2017 |
Barcelona Open BancSabadell
|
1/16 | Feliciano Lopez |
2-6
2-6 |
| 2017 |
Barcelona Open BancSabadell
|
1/32 | Albert Montanes |
4-6
4-6 |
| 2017 |
Sophia Antipolis
|
1/16 | Stefano Napolitano |
2-6
1-6 |
| 2017 |
Open 13 Provence, Qualification
|
Quarter Finals | Andrey Rublev |
6-3
6-2 |
| 2017 |
Open 13 Provence, Qualification
|
1/8 | Albert Montanes |
0-6
6-4 6-4 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Roland Garros ATP
|
1/32 | Novak Djokovic |
6-1
6-2 6-2 |
| 2020 |
Roland Garros ATP
|
1/64 | Richard Berankis |
1-6
4-6 4-6 |
| 2020 |
US Open ATP
|
1/16 | Pablo Carreno Busta |
6-4
6-3 6-2 |
| 2020 |
US Open ATP
|
1/32 | Richard Berankis |
7-5
6-2 1-6 7-6 |
| 2020 |
US Open ATP
|
1/64 | Richard Berankis |
6-7
6-4 4-6 4-6 |
