The No. 1-ranked Serb never faced a break point in his first match in the Italian capital.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2015 |
Roland Garros WTA
|
1/32 | Kristina Mladenovic |
3-6
5-7 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Western & Southern Open
|
1/16 | Elise Mertens |
1-6
7-6 3-6 |
| 2020 |
Western & Southern Open
|
1/32 | Kristina Mladenovic |
3-6
4-6 |
| 2020 |
Palermo Ladies Open
|
1/16 | Ekaterina Alexandrova |
5-7
6-0 6-1 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 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 |
| 2020 |
Internazionali BNL d'Italia, Qualification
|
1/8 | Danka Kovinic |
6-3
4-6 3-6 |
| 2020 |
Internazionali BNL d'Italia, Qualification
|
1/16 | Danka Kovinic |
2-6
1-6 |
| 2020 |
Istanbul Open
|
Quarter Finals | Eugenie Bouchard |
3-6
6-4 7-5 |
| 2020 |
Istanbul Open
|
1/8 | Danka Kovinic |
6-3
6-4 |
| 2020 |
Istanbul Open
|
1/16 | Danka Kovinic |
5-7
2-6 |
