Djokovic has now won every Masters 1000 title at least two times.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
BGL BNP Paribas Luxembourg Open, Qualification
|
1/16 | Kaja Juvan |
3-6
1-6 |
| 2008 |
Qatar Telecom German Open
Germany, Berlin |
Championship | Caroline Wozniacki |
7-6
6-2 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
European Open
|
Quarter Finals | Grigor Dimitrov | |
| 2020 |
European Open
|
1/8 | Milos Raonic |
5-7
6-7 |
| 2020 |
European Open
|
1/16 | Milos Raonic |
3-6
6-7 |
| 2020 |
St. Petersburg Open
|
Semi Finals | Borna Coric |
1-6
6-1 6-4 |
| 2020 |
St. Petersburg Open
|
Quarter Finals | Milos Raonic |
1-6
6-7 |
| 2020 |
St. Petersburg Open
|
1/8 | Milos Raonic |
3-6
2-6 |
| 2020 |
St. Petersburg Open
|
1/16 | Milos Raonic |
6-7
1-6 |
| 2020 |
Internazionali BNL d'Italia
|
1/16 | Dusan Lajovic |
6-7
6-4 2-6 |
| 2020 |
Internazionali BNL d'Italia
|
1/32 | Milos Raonic |
7-6
6-2 |
