| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2009 |
Australian Open
Australia, Victoria, Melbourne |
Championship | Novak Djokovic |
2-6
6-4 3-6 6-7 |
| 2007 |
Wimbledon
|
Championship | Novak Djokovic |
3-6
6-3 3-6 6-7 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Shanghai Rolex Masters
|
Quarter Finals | Stefanos Tsitsipas |
6-3
5-7 3-6 |
| 2019 |
Shanghai Rolex Masters
|
1/8 | Novak Djokovic |
7-5
6-3 |
| 2019 |
Shanghai Rolex Masters
|
1/16 | Novak Djokovic |
6-3
6-3 |
| 2019 |
Rakuten Japan Open Tennis Championships
|
Final | Novak Djokovic |
6-3
6-2 |
| 2019 |
Rakuten Japan Open Tennis Championships
|
Semi Finals | Novak Djokovic |
6-3
6-4 |
| 2019 |
Rakuten Japan Open Tennis Championships
|
Quarter Finals | Novak Djokovic |
6-1
6-2 |
| 2019 |
Rakuten Japan Open Tennis Championships
|
1/8 | Novak Djokovic |
6-3
7-5 |
| 2019 |
Rakuten Japan Open Tennis Championships
|
1/16 | Novak Djokovic |
6-4
6-2 |
| 2019 |
US Open ATP
|
1/8 | Stan Wawrinka |
4-6
5-7 1-2 |
| 2019 |
US Open ATP
|
1/16 | Novak Djokovic |
6-3
6-4 6-2 |
| 2019 |
US Open ATP
|
1/32 | Novak Djokovic |
6-4
7-6 6-1 |
| 2019 |
US Open ATP
|
1/64 | Novak Djokovic |
6-4
6-1 6-4 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2012 |
Nottingham, Qualification
|
1/16 | Pierre-Hugues Herbert |
4-6
4-6 |
| 2012 |
Roland Garros, Qualification
|
1/64 | Ruben Bemelmans |
6-7
2-6 |
