The Serb and the Spaniard will both face Top 10 opposition in the round-robin stage.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2017 |
VTB Kremlin Cup, Qualification
|
Quarter Finals | Kaia Kanepi |
6-2
2-6 7-6 |
| 2017 |
VTB Kremlin Cup, Qualification
|
1/8 | Alisa Kleybanova |
6-4
6-2 |
| 2017 |
VTB Kremlin Cup, Qualification
|
1/16 | Alisa Kleybanova |
6-2
6-3 |
| 2014 |
Wimbledon WTA
|
1/64 | Lauren Davis |
6-1
6-2 |
| 2014 |
Roland Garros WTA
|
1/64 | Simona Halep |
0-6
2-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Nitto ATP World Tour Finals Final Stage
|
Semi Finals | Dominic Thiem |
7-5
6-7 7-6 |
| 2020 |
Nitto ATP World Tour Finals, Group Tokyo 1970
|
Championship | Novak Djokovic |
6-3
7-6 |
| 2020 |
Nitto ATP World Tour Finals, Group Tokyo 1970
|
Championship | Daniil Medvedev |
3-6
3-6 |
| 2020 |
Nitto ATP World Tour Finals, Group Tokyo 1970
|
Championship | Novak Djokovic |
6-3
6-2 |
| 2020 |
Erste Bank Open
|
Quarter Finals | Lorenzo Sonego |
2-6
1-6 |
| 2020 |
Erste Bank Open
|
1/8 | Novak Djokovic |
7-6
6-3 |
| 2020 |
Erste Bank Open
|
1/16 | Novak Djokovic |
7-6
6-3 |
