| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Roland Garros ATP
|
1/64 | Grigor Dimitrov |
3-6
0-6 6-3 7-6 4-6 |
| 2019 |
Australian Open ATP
|
1/64 | Grigor Dimitrov |
4-6
6-3 6-1 6-4 |
| 2016 |
AEGON Championships
England, London |
1/16 | Janko Tipsarevic |
6-7
6-4 3-6 |
| 2013 |
Monte Carlo Rolex Masters
Monaco, Monte Carlo |
1/16 | Grigor Dimitrov |
6-7
1-6 |
| 2012 |
Sony Ericsson Open
United States, Florida, Miami |
1/8 | Janko Tipsarevic |
6-7
2-6 |
| 2011 |
Legg Mason Tennis Classic
United States, District of Columbia, Washington |
Championship | Janko Tipsarevic |
4-6
2-6 |
| 2011 |
AEGON International
England, Eastbourne |
Championship | Janko Tipsarevic |
6-3
7-6 |
| 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 |
| year | Event | RND | Winner | Results |
|---|
