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 |
|---|---|---|---|---|
| 2020 |
Australian Open ATP
|
Semi Finals | Novak Djokovic |
6-7
4-6 3-6 |
| 2020 |
Australian Open ATP
|
Quarter Finals | Roger Federer |
3-6
6-2 6-2 6-7 3-6 |
| 2020 |
Australian Open ATP
|
1/8 | Roger Federer |
6-4
1-6 2-6 2-6 |
| 2020 |
Australian Open ATP
|
1/16 | Roger Federer |
6-4
6-7 4-6 6-4 6-7 |
| 2020 |
Australian Open ATP
|
1/32 | Roger Federer |
1-6
4-6 1-6 |
| 2020 |
Australian Open ATP
|
1/64 | Roger Federer |
3-6
2-6 2-6 |
| 2019 |
Nitto ATP World Tour Finals Final Stage
|
Championship | Stefanos Tsitsipas |
6-3
6-4 |
| 2019 |
Nitto ATP World Tour Finals, Group Bjorn Borg
|
Championship | Roger Federer |
4-6
3-6 |
| 2019 |
Nitto ATP World Tour Finals, Group Bjorn Borg
|
Championship | Roger Federer |
7-6
6-3 |
| 2019 |
Nitto ATP World Tour Finals, Group Bjorn Borg
|
Championship | Dominic Thiem |
5-7
5-7 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2013 |
Generali Ladies Linz presented by voestalpine, Qualification
|
1/16 | Camila Giorgi |
6-2
6-2 |
| 2013 |
Budapest Grand Prix
|
1/16 | Agnes Bukta |
1-6
6-4 6-7 |
| 2013 |
Wimbledon, Qualification WTA
|
1/48 (Special Qual) | Sesil Karatantcheva |
6-1
5-7 4-6 |
