World No. 1 Djokovic will face his talented compatriot in a rematch of an Adria Tour loss.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2015 |
Szczecin
|
Quarter Finals | Nicolas Almagro |
5-7
1-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
Szczecin
|
1/16 | Facundo Arguello |
7-5
2-1 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Internazionali BNL d'Italia
|
1/8 | Novak Djokovic |
7-6
6-3 |
| 2020 |
Internazionali BNL d'Italia
|
1/16 | Filip Krajinovic |
4-6
1-6 |
| 2020 |
Internazionali BNL d'Italia
|
1/32 | Filip Krajinovic |
6-4
7-5 |
| 2020 |
US Open ATP
|
1/16 | David Goffin |
1-6
6-7 4-6 |
| 2020 |
US Open ATP
|
1/32 | Filip Krajinovic |
6-4
6-1 6-3 |
| 2020 |
US Open ATP
|
1/64 | Filip Krajinovic |
6-2
7-6 6-3 |
| 2020 |
Western & Southern Open
|
Quarter Finals | Milos Raonic |
4-6
7-6 7-5 |
| 2020 |
Western & Southern Open
|
1/8 | Filip Krajinovic |
2-6
1-6 |
| 2020 |
Western & Southern Open
|
1/16 | Filip Krajinovic |
6-2
6-1 |
| 2020 |
Western & Southern Open
|
1/32 | Filip Krajinovic |
7-5
6-4 |
