The Serb won his US Open first-rounder on Monday night over Damir Dzumhur.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Roland Garros WTA
|
1/64 | Aryna Sabalenka |
7-5
6-1 |
| 2019 |
Italian Open
|
1/16 | Naomi Osaka |
6-3
6-3 |
| 2019 |
Italian Open
|
1/32 | Dominika Cibulkova |
2-6
3-6 |
| 2019 |
Madrid Open
|
1/32 | Naomi Osaka |
6-2
7-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Internazionali BNL d'Italia, Qualification
|
1/8 | Federico Coria |
1-6
1-6 |
| 2020 |
Internazionali BNL d'Italia, Qualification
|
1/16 | Damir Dzumhur |
7-5
6-4 |
| 2020 |
Internazionali BNL d'Italia, Qualification
|
1/32 | Damir Dzumhur |
0-6
2-6 |
| 2020 |
US Open ATP
|
1/64 | Novak Djokovic |
6-1
6-4 6-1 |
| 2020 |
Western & Southern Open, Qualification
|
1/24 (Special Qual) | Dennis Novak |
7-5
1-6 4-6 |
