Grigor Dimitrov (Bulgaria) 1 - 13 Novak Djokovic (Serbia)
| Date | Tournament | Rnd | Winner | Score |
|---|---|---|---|---|
| 29 Mar 2025 |
Miami Open
Miami, Florida,
USA
ATP Tour Masters, Hard |
SF |
Novak Djokovic
(SRB  )
|
2-6 3-6 |
| 05 Nov 2023 |
Rolex Paris Masters
Paris,
France
ATP Tour Masters, Hard |
F |
Novak Djokovic
(SRB )
|
4-6 3-6 |
| 14 May 2023 |
Internazionali BNL d'Italia
Rome,
Italy
ATP Tour Masters, Clay |
R32 |
Novak Djokovic
(SRB )
|
3-6 6-4 1-6 |
| 21 Jan 2023 |
Australian Open
Melbourne,
Australia
Grand Slam, Hard |
R32 |
Novak Djokovic
(SRB )
|
6-7(7) 3-6 4-6 |
| 02 Nov 2019 |
Rolex Paris Masters
Paris,
France
ATP Tour Masters, Hard |
SF |
Novak Djokovic
(SRB )
|
6-7(5) 4-6 |
| 16 Aug 2018 |
Cincinnati Open
Cincinnati, OH,
USA
ATP Tour Masters, Hard |
R16 |
Novak Djokovic
(SRB )
|
6-2 3-6 4-6 |
| 21 Jun 2018 |
HSBC Championships
London / Queen`s Club,
Great Britain
ATP Tour 500, Grass |
R16 |
Novak Djokovic
(SRB )
|
4-6 1-6 |
| 03 Nov 2016 |
Rolex Paris Masters
Paris,
France
ATP Tour Masters, Hard |
R16 |
Novak Djokovic
(SRB )
|
6-4 2-6 3-6 |
| 03 Oct 2014 |
China Open
Beijing,
China
ATP Tour 500, Hard |
Q |
Novak Djokovic
(SRB )
|
2-6 4-6 |
| 04 Jul 2014 |
The Championships
Wimbledon,
Great Britain
Grand Slam, Grass |
SF |
Novak Djokovic
(SRB )
|
4-6 6-3 6-7(2) 6-7(7) |
| 01 Jun 2013 |
Roland Garros
Paris,
France
Grand Slam, Clay |
R32 |
Novak Djokovic
(SRB )
|
2-6 2-6 3-6 |
| 07 May 2013 |
Mutua Madrid Open
Madrid,
Spain
ATP Tour Masters, Clay |
R32 |
Grigor Dimitrov
(BUL  )
|
7-6(6) 6-7(8) 6-3 |
| 12 Mar 2013 |
BNP Paribas Open
Indian Wells, CA,
USA
ATP Tour Masters, Hard |
R32 |
Novak Djokovic
(SRB )
|
6-7(4) 1-6 |
| 10 Oct 2012 |
Shanghai Rolex Masters
Shanghai,
China
ATP Tour Masters, Hard |
R32 |
Novak Djokovic
(SRB )
|
3-6 2-6 |