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 |
|---|---|---|---|---|
| 2016 |
Open BancSabadell
|
1/8 | Rafael Nadal |
6-2
6-2 |
| 2014 |
Rio Open presented by Claro hdtv
|
1/8 | Rafael Nadal |
6-1
6-2 |
| 2007 |
Roland Garros
France, Paris |
Championship | Rafael Nadal |
1-6
3-6 2-6 |
| 2005 |
Abierto Mexicano Telcel
|
Championship | Rafael Nadal |
6-1
6-0 |
| 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 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2017 |
Barcelona Open BancSabadell
|
1/16 | Feliciano Lopez |
2-6
2-6 |
| 2017 |
Barcelona Open BancSabadell
|
1/32 | Albert Montanes |
4-6
4-6 |
| 2017 |
Sophia Antipolis
|
1/16 | Stefano Napolitano |
2-6
1-6 |
| 2017 |
Open 13 Provence, Qualification
|
Quarter Finals | Andrey Rublev |
6-3
6-2 |
| 2017 |
Open 13 Provence, Qualification
|
1/8 | Albert Montanes |
0-6
6-4 6-4 |
