| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
China Open
|
Championship | ||
| 2017 |
Shanghai Rolex Masters
|
1/16 | Grigor Dimitrov |
6-3
3-6 6-7 |
| 2017 |
AEGON Championships
|
1/16 | Grigor Dimitrov |
6-3
6-1 |
| 2015 |
Abierto Mexicano Telcel
|
1/8 | Ryan Harrison |
7-5
4-6 6-0 |
| 2014 |
US Open
|
1/64 | Grigor Dimitrov |
6-2
7-6 6-2 |
| 2014 |
Wimbledon
|
1/64 | Grigor Dimitrov |
7-6
6-3 6-2 |
| 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 |
Delray Beach Open
|
1/16 | Ryan Harrison |
6-3
6-2 |
| 2020 |
Cleveland
|
1/16 | Ryan Harrison |
6-3
6-7 6-3 |
