The Serb won his fourth title of the year after one of the lowest moments of his career.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Internazionali BNL d'Italia
|
1/32 | Danka Kovinic |
1-6
0-6 |
| 2020 |
Qatar Total Open
|
1/32 | Maria Sakkari |
6-4
6-3 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Internazionali BNL d'Italia
|
Final | Novak Djokovic |
7-5
6-3 |
| 2020 |
Internazionali BNL d'Italia
|
Semi Finals | Novak Djokovic |
7-5
6-3 |
| 2020 |
Internazionali BNL d'Italia
|
Quarter Finals | Novak Djokovic |
6-3
4-6 6-3 |
| 2020 |
Internazionali BNL d'Italia
|
1/8 | Novak Djokovic |
7-6
6-3 |
| 2020 |
Internazionali BNL d'Italia
|
1/16 | Novak Djokovic |
6-3
6-2 |
| 2020 |
US Open ATP
|
1/8 | Pablo Carreno Busta |
5-6
|
| 2020 |
US Open ATP
|
1/16 | Novak Djokovic |
6-3
6-3 6-1 |
| 2020 |
US Open ATP
|
1/32 | Novak Djokovic |
6-7
6-3 6-4 6-2 |
| 2020 |
US Open ATP
|
1/64 | Novak Djokovic |
6-1
6-4 6-1 |
| 2020 |
Western & Southern Open
|
Final | Novak Djokovic |
1-6
6-3 6-4 |
| 2020 |
Western & Southern Open
|
Semi Finals | Novak Djokovic |
4-6
6-4 7-6 |
| 2020 |
Western & Southern Open
|
Quarter Finals | Novak Djokovic |
6-3
6-1 |
| 2020 |
Western & Southern Open
|
1/8 | Novak Djokovic |
6-2
6-4 |
| 2020 |
Western & Southern Open
|
1/16 | Novak Djokovic |
7-6
6-4 |
