Djokovic has now won every Masters 1000 title at least two times.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2015 |
ABN AMRO World Tennis Tournament
|
Quarter Finals | Milos Raonic |
6-2
3-6 4-6 |
| 2012 |
R. M. Keegan Championships
|
1/8 | Milos Raonic |
4-6
4-6 |
| 2010 |
Malaysian Open
Malaysia, Kuala Lumpur |
Championship | Milos Raonic |
7-6
6-7 3-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Ostrava
|
1/8 | Mats Moraign |
6-1
6-7 4-0 |
| 2020 |
Ostrava
|
1/16 | Sergiy Stakhovsky |
6-4
4-6 3-6 |
| 2020 |
Prague 2
|
1/16 | Sergiy Stakhovsky |
6-2
6-7 6-7 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 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 |
| 2020 |
US Open ATP
|
1/32 | Vasek Pospisil |
6-7
6-3 7-6 6-3 |
| 2020 |
US Open ATP
|
1/64 | Milos Raonic |
3-6
2-6 3-6 |
| 2020 |
Western & Southern Open
|
Final | Novak Djokovic |
1-6
6-3 6-4 |
| 2020 |
Western & Southern Open
|
Semi Finals | Milos Raonic |
6-7
3-6 |
| 2020 |
Western & Southern Open
|
Quarter Finals | Milos Raonic |
4-6
7-6 7-5 |
| 2020 |
Western & Southern Open
|
1/8 | Milos Raonic |
2-6
2-6 |
| 2020 |
Western & Southern Open
|
1/16 | Milos Raonic |
6-3
7-5 |
| 2020 |
Western & Southern Open
|
1/32 | Milos Raonic |
4-6
4-6 |
