The No. 1-ranked Serb never faced a break point in his first match in the Italian capital.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Parma
|
1/8 | Marco Cecchinato |
7-5
6-3 |
| 2020 |
Parma
|
1/16 | Philipp Kohlschreiber |
3-6
1-6 |
| 2020 |
Roland Garros ATP
|
1/64 | Cristian Garin |
6-4
4-6 6-1 6-4 |
| 2020 |
Hamburg European Open
|
1/16 | Fabio Fognini |
6-4
1-6 5-7 |
| 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 |
