| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2016 |
China Open
China, Beijing |
1/8 | Grigor Dimitrov |
7-6
6-7 4-6 |
| 2013 |
Roland Garros
|
1/32 | Grigor Dimitrov |
1-6
6-7 1-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Mexican Open
|
Semi Finals | Rafael Nadal |
6-3
6-2 |
| 2020 |
Mexican Open
|
Quarter Finals | Grigor Dimitrov |
4-6
4-6 |
| 2020 |
Mexican Open
|
1/8 | Grigor Dimitrov |
7-6
2-6 6-7 |
| 2020 |
Mexican Open
|
1/16 | Grigor Dimitrov |
3-6
3-6 |
| 2020 |
Rotterdam Open
|
1/8 | Felix Auger-Aliassime |
4-6
2-6 |
| 2020 |
Rotterdam Open
|
1/16 | Grigor Dimitrov |
3-6
6-7 |
| 2020 |
Open Sud de France
|
1/8 | Gregoire Barrere |
7-6
4-6 5-7 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Indian Wells
|
1/16 | Noah Rubin |
6-4
7-6 |
| 2019 |
Shanghai Rolex Masters
|
1/16 | John Isner |
5-7
3-6 |
| 2019 |
Shanghai Rolex Masters
|
1/32 | Lucas Pouille |
7-6
4-6 4-6 |
| 2019 |
Rakuten Japan Open Tennis Championships
|
Quarter Finals | Novak Djokovic |
6-1
6-2 |
| 2019 |
Rakuten Japan Open Tennis Championships
|
1/8 | Lucas Pouille |
1-6
2-6 |
| 2019 |
Rakuten Japan Open Tennis Championships
|
1/16 | Lucas Pouille |
4-6
3-6 |
