Djokovic advanced in his first meeting with Sinner, who reached the Miami Open final.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Barcelona Open
|
1/16 | Diego Schwartzman |
3-6
7-5 6-1 |
| 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 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2015 |
US Open, Qualification WTA
|
1/64 | Mayo Hibi |
6-3
1-6 2-6 |
| 2015 |
Wimbledon WTA
|
1/64 | Urszula Radwanska |
2-6
1-6 |
| 2015 |
Family Circle Cup
|
1/32 | Madison Brengle |
7-6
4-6 2-6 |
