Djokovic advanced in his first meeting with Sinner, who reached the Miami Open final.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Bavarian International Tennis Championships
|
1/16 | Diego Schwartzman |
4-6
6-1 1-6 |
| 2018 |
Internazionali BNL d'Italia
|
1/16 | Benoit Paire |
6-2
4-6 2-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Monte Carlo Masters
|
1/16 | Casper Ruud |
3-6
3-6 |
| 2021 |
Miami Open
|
1/8 | Sebastian Korda |
3-6
6-4 5-7 |
| 2021 |
Miami Open
|
1/16 | Diego Schwartzman |
6-1
6-4 |
| 2021 |
Miami Open
|
1/32 | Diego Schwartzman |
6-3
6-3 |
| 2021 |
Mexican Open
|
1/16 | Lorenzo Musetti |
3-6
6-2 4-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Monte Carlo Masters
|
1/32 | Jordan Thompson |
6-4
6-7 7-6 |
| 2021 |
Miami Open
|
1/32 | Lorenzo Musetti |
6-3
6-3 |
