The No. 1-ranked Serb never faced a break point in his first match in the Italian capital.
| 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 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Phillip Island Trophy
|
1/32 | Marie Bouzkova |
3-6
5-0 |
| 2021 |
Australian Open WTA
|
1/64 | Ashleigh Barty |
6-0
6-0 |
| 2021 |
Gippsland Trophy
|
1/16 | Jelena Ostapenko |
6-4
7-5 |
| 2021 |
Gippsland Trophy
|
1/32 | Danka Kovinic |
6-3
6-3 |
