Djokovic advanced in his first meeting with Sinner, who reached the Miami Open final.
| 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 |
|---|---|---|---|---|
| 2014 |
Roland Garros WTA
|
1/64 | CoCo Vandeweghe |
6-7
2-6 |
| 2014 |
Nurnberger Versicherungscup
|
1/16 | Elina Svitolina |
7-5
6-4 |
| 2014 |
Sony Open Tennis
United States, Florida, Miami |
Championship | Alisa Kleybanova |
6-7
1-6 |
