The Serb tied Roger Federer for second-most wins for a man in French Open history.
| 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 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Volvo Car Open, Qualification
|
1/16 | Nicole Melichar |
6-7
7-6 6-3 |
| 2019 |
Fed Cup World Group 2
|
Championship | Kurumi Nara |
7-6
6-4 |
| 2019 |
Australian Open, Qualification WTA
|
1/64 | Olga Govortsova |
6-2
2-6 1-6 |
