| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2015 |
Australian Open
|
1/32 | Grigor Dimitrov |
3-6
7-6 3-6 3-6 |
| 2010 |
Orleans
|
Championship | Grigor Dimitrov |
5-7
3-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Pau
|
1/8 | Quentin Halys |
6-7
2-6 |
| 2020 |
Open 13 Provence, Qualification
|
1/8 | Emil Ruusuvuori |
4-6
4-6 |
| 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 |
