The Bulgarian has been a semifinalist at the Australian Open, Wimbledon and the US Open.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2011 |
Open de Moselle
France, Metz |
Championship | Igor Sijsling |
6-2
6-2 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Helsinki
|
1/32 | Jaroslav Pospisil |
7-5
6-2 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Internazionali BNL d'Italia
|
Quarter Finals | Denis Shapovalov |
6-2
3-6 6-2 |
| 2020 |
Internazionali BNL d'Italia
|
1/8 | Grigor Dimitrov |
4-6
6-4 6-4 |
| 2020 |
Internazionali BNL d'Italia
|
1/16 | Grigor Dimitrov |
6-1
6-0 |
| 2020 |
Internazionali BNL d'Italia
|
1/32 | Grigor Dimitrov |
7-5
6-1 |
| 2020 |
US Open ATP
|
1/32 | Marton Fucsovics |
7-6
6-7 6-3 4-6 1-6 |
| 2020 |
US Open ATP
|
1/64 | Grigor Dimitrov |
6-4
6-3 6-1 |
| 2020 |
Western & Southern Open
|
1/16 | Marton Fucsovics |
5-7
6-4 2-6 |
| 2020 |
Western & Southern Open
|
1/32 | Grigor Dimitrov |
6-3
6-4 |
