| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
Australian Open ATP
|
1/8 | Grigor Dimitrov |
7-6
7-6 4-6 7-6 |
| 2018 |
Brisbane International
|
Semi Finals | Nick Kyrgios |
6-3
1-6 4-6 |
| 2017 |
Western & Southern Open
|
Final | Grigor Dimitrov |
3-6
5-7 |
| 2015 |
BNP Paribas Open
|
1/32 | Grigor Dimitrov |
6-7
6-3 6-7 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Davis Cup Finals, Group D
|
Championship | Nick Kyrgios |
2-6
6-7 |
| 2019 |
Davis Cup Finals, Group D
|
Championship | Nick Kyrgios |
6-4
6-4 |
| 2019 |
Zhuhai Championships
|
1/16 | Andreas Seppi |
6-7
1-6 |
| 2019 |
Laver Cup
|
Championship | Roger Federer |
6-7
7-5 10-7 |
| 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 |
