| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2016 |
Abierto Mexicano Telcel
|
1/8 | Grigor Dimitrov |
6-3
6-4 |
| 2015 |
Mutua Madrid Open
|
1/32 | Grigor Dimitrov |
6-4
3-0 |
| 2014 |
Rogers Cup
|
1/16 | Grigor Dimitrov |
6-4
2-6 3-6 |
| 2012 |
Roland Garros
|
1/64 | Grigor Dimitrov |
6-7
1-6 1-6 |
| 2012 |
R. M. Keegan Championships
|
1/16 | Donald Young |
6-7
6-4 6-7 |
| 2011 |
Winston-Salem
|
Championship | Grigor Dimitrov |
6-4
2-6 7-6 |
| 2010 |
Honolulu
|
Championship | Donald Young |
6-4
7-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Rolex Paris Masters
|
Semi Finals | Novak Djokovic |
7-6
6-4 |
| 2019 |
Rolex Paris Masters
|
Quarter Finals | Grigor Dimitrov |
2-6
5-7 |
| 2019 |
Rolex Paris Masters
|
1/8 | Grigor Dimitrov |
6-3
6-2 |
| 2019 |
Rolex Paris Masters
|
1/16 | Grigor Dimitrov |
5-7
3-6 |
| 2019 |
Rolex Paris Masters
|
1/32 | Grigor Dimitrov |
4-6
6-1 6-2 |
| 2019 |
Erste Bank Open
|
1/8 | Matteo Berrettini |
7-6
7-6 |
| 2019 |
Erste Bank Open
|
1/16 | Grigor Dimitrov |
6-3
7-5 |
| 2019 |
Intrum Stockholm Open
|
1/8 | Sam Querrey |
6-7
6-3 7-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Knoxville
|
1/32 | Liam Broady |
7-6
6-3 |
| 2019 |
Charlottesville
|
1/32 | Blaz Kavcic |
3-6
6-7 |
