Grigor Dimitrov (Bulgaria) 1 - 12 Novak Djokovic (Serbia)

Date	Tournament	Surface	Rd	Opp. Rank	Winner	Score
05 Nov 2023	Rolex Paris Masters Paris, France ATP Tour Masters	Hard	F	1	Novak Djokovic (SRB)	4-6 3-6
14 May 2023	Internazionali BNL d'Italia Rome, Italy ATP Tour Masters	Clay	R32	1	Novak Djokovic (SRB)	3-6 6-4 1-6
21 Jan 2023	Australian Open Melbourne, Australia Grand Slam	Hard	R32	5	Novak Djokovic (SRB)	6-7(7) 3-6 4-6
02 Nov 2019	Rolex Paris Masters Paris, France ATP Tour Masters	Hard	SF	1	Novak Djokovic (SRB)	6-7(5) 4-6
16 Aug 2018	W & S Open Cincinnati, OH, USA ATP Tour Masters	Hard	R16	10	Novak Djokovic (SRB)	6-2 3-6 4-6
21 Jun 2018	cinch Championships London / Queen`s Club, Great Britain ATP Tour 500	Grass	R16	22	Novak Djokovic (SRB)	4-6 1-6
03 Nov 2016	Rolex Paris Masters Paris, France ATP Tour Masters	Hard	R16	1	Novak Djokovic (SRB)	6-4 2-6 3-6
03 Oct 2014	China Open Beijing, China ATP Tour 500	Hard	Q	1	Novak Djokovic (SRB)	2-6 4-6
04 Jul 2014	The Championships Wimbledon, Great Britain Grand Slam	Grass	SF	2	Novak Djokovic (SRB)	4-6 6-3 6-7(2) 6-7(7)
01 Jun 2013	Roland Garros Paris, France Grand Slam	Clay	R32	1	Novak Djokovic (SRB)	2-6 2-6 3-6
07 May 2013	Mutua Madrid Open Madrid, Spain ATP Tour Masters	Clay	R32	1	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	1	Novak Djokovic (SRB)	6-7(4) 1-6
10 Oct 2012	Shanghai Rolex Masters Shanghai, China ATP Tour Masters	Hard	R32	2	Novak Djokovic (SRB)	3-6 2-6