The No. 1-ranked Serb never faced a break point in his first match in the Italian capital.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2014 |
China Open
|
1/32 | Tsvetana Pironkova |
4-6
1-6 |
| 2014 |
KDB Korea Open
|
Semi Finals | Karolina Pliskova |
6-4
6-7 3-6 |
| 2014 |
KDB Korea Open
|
Quarter Finals | Maria Kirilenko |
7-6
2-6 3-6 |
| 2014 |
KDB Korea Open
|
1/8 | Maria Kirilenko |
6-7
6-4 6-0 |
| 2014 |
KDB Korea Open
|
1/16 | Maria Kirilenko |
3-6
6-2 6-4 |
| 2014 |
US Open WTA
|
1/64 | Maria Sharapova |
6-4
6-0 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Internazionali BNL d'Italia
|
1/8 | Casper Ruud |
6-2
7-6 |
| 2020 |
Internazionali BNL d'Italia
|
1/16 | Marin Cilic |
6-2
6-2 |
| 2020 |
Internazionali BNL d'Italia
|
1/32 | Marin Cilic |
6-7
6-2 6-4 |
| 2020 |
US Open ATP
|
1/16 | Dominic Thiem |
2-6
2-6 6-3 3-6 |
| 2020 |
US Open ATP
|
1/32 | Marin Cilic |
6-3
1-6 7-6 7-5 |
| 2020 |
US Open ATP
|
1/64 | Marin Cilic |
6-7
3-6 7-5 7-5 6-3 |
| 2020 |
Western & Southern Open
|
1/32 | Denis Shapovalov |
6-3
6-3 |
