The No. 1-ranked Serb never faced a break point in his first match in the Italian capital.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 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 |
| 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 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2015 |
Lexington
|
1/8 | Mitchell Krueger |
1-6
1-6 |
| 2015 |
Lexington
|
1/16 | Ryan Sweeting |
7-6
6-2 |
| 2015 |
Binghamton
|
1/16 | Edward Corrie |
5-7
2-6 |
