| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2017 |
Mutua Madrid Open
|
1/16 | Grigor Dimitrov |
6-3
7-5 |
| 2016 |
Rogers Cup
Canada, Ontario, Toronto |
1/8 | Grigor Dimitrov |
3-6
5-7 |
| 2016 |
Istanbul Open
|
Semi Finals | Grigor Dimitrov |
6-7
6-7 |
| 2014 |
Roland Garros
|
1/64 | Ivo Karlovic |
4-6
5-7 6-7 |
| 2014 |
Internazionali BNL d'Italia
|
1/16 | Grigor Dimitrov |
7-6
6-4 |
| 2013 |
PBZ Zagreb Indoors
Croatia, Zagreb |
1/16 | Ivo Karlovic |
7-6
7-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Intrum Stockholm Open
|
1/8 | Sam Querrey |
6-7
6-3 7-6 |
| 2019 |
China Open
|
1/16 | Andrey Rublev |
2-6
5-7 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Swiss Indoors Basel, Qualification
|
1/8 | Peter Gojowczyk |
6-2
6-4 |
| 2019 |
VTB Kremlin Cup
|
1/8 | Marin Cilic |
6-1
7-6 |
| 2019 |
VTB Kremlin Cup
|
1/16 | Ivo Karlovic |
6-4
6-7 7-6 |
| 2019 |
US Open ATP
|
1/64 | Frances Tiafoe |
2-6
3-6 2-1 |
