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 |
|---|---|---|---|---|
| 2021 |
Australian Open WTA
|
Quarter Finals | Naomi Osaka |
2-6
2-6 |
| 2021 |
Australian Open WTA
|
1/8 | Hsieh Su-wei |
6-4
6-2 |
| 2021 |
Australian Open WTA
|
1/16 | Hsieh Su-wei |
6-4
2-6 7-5 |
| 2021 |
Australian Open WTA
|
1/32 | Hsieh Su-wei |
3-6
2-6 |
| 2021 |
Australian Open WTA
|
1/64 | Hsieh Su-wei |
7-5
6-2 |
| 2021 |
Yarra Valley Classic
|
1/32 | Alison van Uytvanck |
2-6
0-6 |
| 2021 |
Abu Dhabi WTA Women’s Tennis Open
|
1/32 | Hsieh Su-wei |
6-3
3-6 6-7 |
