Initially rising to No. 1 on July 4, 2011, the Serb has spent 64.26% of the time on top.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Dubai Duty Free Tennis Championships
|
1/32 | Alize Cornet |
6-4
3-6 6-1 |
| 2021 |
Phillip Island Trophy
|
1/32 | Kimberly Birrell |
6-2
7-5 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Australian Open ATP
|
Quarter Finals | Stefanos Tsitsipas |
3-6
2-6 7-6 6-4 7-5 |
| 2021 |
Australian Open ATP
|
1/8 | Rafael Nadal |
3-6
4-6 2-6 |
| 2021 |
Australian Open ATP
|
1/16 | Rafael Nadal |
5-7
2-6 5-7 |
| 2021 |
Australian Open ATP
|
1/32 | Rafael Nadal |
1-6
4-6 2-6 |
| 2021 |
Australian Open ATP
|
1/64 | Rafael Nadal |
3-6
4-6 1-6 |
| 2020 |
Nitto ATP World Tour Finals Final Stage
|
Semi Finals | Daniil Medvedev |
3-6
7-6 6-3 |
