| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2016 |
Apia International Sydney
|
Quarter Finals | Grigor Dimitrov |
6-4
3-6 4-6 |
| 2015 |
Rogers Cup
|
1/32 | Grigor Dimitrov |
4-6
5-7 |
| 2014 |
Wimbledon
|
1/16 | Grigor Dimitrov |
6-7
6-4 2-6 6-4 6-1 |
| 2014 |
AEGON Championships
|
Quarter Finals | Grigor Dimitrov | |
| 2013 |
Swiss Indoors Basel
|
1/8 | Grigor Dimitrov |
6-3
6-2 |
| 2011 |
Winston-Salem
|
Championship | Alexandr Dolgopolov |
4-6
6-1 6-7 |
| 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 |
|---|---|---|---|---|
| 2018 |
Internazionali BNL d'Italia
|
1/32 | Novak Djokovic |
6-1
6-3 |
