The No. 1-ranked Serb never faced a break point in his first match in the Italian capital.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2016 |
Davis Cup Group 2 - Europe/Africa
|
Championship | Jarkko Nieminen |
3-6
6-3 1-6 6-7 |
| 2015 |
if...Stockholm Open
|
1/16 | Nicolas Almagro |
3-6
7-6 6-4 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Abu Dhabi WTA Women’s Tennis Open
|
1/32 | Karolina Muchova |
6-4
6-1 |
| 2020 |
Roland Garros WTA
|
1/64 | Victoria Azarenka |
6-1
6-2 |
| 2020 |
Internazionali BNL d'Italia
|
1/8 | Elise Mertens |
4-6
4-6 |
| 2020 |
Internazionali BNL d'Italia
|
1/16 | Danka Kovinic |
3-6
1-6 |
| 2020 |
Internazionali BNL d'Italia
|
1/32 | Danka Kovinic |
1-6
0-6 |
