Djokovic has now won every Masters 1000 title at least two times.
| 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 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2014 |
Wimbledon WTA
|
1/16 | Barbora Strycova |
7-6
7-6 |
| 2014 |
Wimbledon WTA
|
1/32 | Na Li |
2-6
2-6 |
| 2014 |
Wimbledon WTA
|
1/64 | Na Li |
5-7
2-6 |
| 2014 |
Roland Garros WTA
|
1/64 | Kristina Mladenovic |
7-5
3-6 6-1 |
