| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2017 |
Wimbledon
|
1/16 | Grigor Dimitrov |
6-1
6-1 0-0 |
| 2016 |
Delray Beach International Tennis Championships
|
1/16 | Grigor Dimitrov |
4-6
2-6 |
| 2014 |
US Open
|
1/32 | Grigor Dimitrov |
6-1
6-2 6-2 |
| 2013 |
AEGON Championships
England, London |
1/32 | Grigor Dimitrov |
6-4
2-6 6-7 |
| 2012 |
Open de Nice Côte d’Azur
|
1/16 | Grigor Dimitrov |
5-7
1-6 |
| 2010 |
Ramat Hasharon
|
Championship | Dudi Sela |
6-4
7-6 |
| 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
|
1/32 | Mitchell Krueger |
0-6
7-6 7-5 |
| 2020 |
Columbus
|
1/16 | Kaichi Uchida |
7-5
1-0 |
