| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2017 |
ABN AMRO World Tennis Tournament
|
1/8 | Grigor Dimitrov |
7-6
6-1 |
| 2017 |
Australian Open
|
1/8 | Grigor Dimitrov |
2-6
7-6 6-2 6-1 |
| 2014 |
Shanghai Rolex Masters
|
1/32 | Grigor Dimitrov |
6-3
6-3 |
| 2009 |
Besancon
|
Championship | Denis Istomin |
6-3
2-6 6-7 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Davis Cup Qualifying Round
|
Championship | Tommy Paul |
6-3
6-0 |
| 2020 |
Davis Cup Qualifying Round
|
Championship | Reilly Opelka |
6-2
7-5 |
| 2020 |
Columbus
|
1/8 | Denis Istomin |
3-6
1-6 |
| 2020 |
Delray Beach Open
|
1/16 | Milos Raonic |
2-6
2-6 |
| 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 |
