Grigor Dimitrov (Bulgaria) 2 - 6 Stefanos Tsitsipas (Greece)

Date	Tournament	Surface	Rd	Opp. Rank	Winner	Score
04 Nov 2023	Rolex Paris Masters Paris, France ATP Tour Masters	Hard	SF	6	Grigor Dimitrov (BUL)	6-3 6-7(1) 7-6(3)
29 Dec 2022	United Cup Perth, Brisbane, Sydney, Australia United Cup	Hard	RR	4	Stefanos Tsitsipas (GRE)	6-4 2-6 6-7(4)
11 May 2022	Internazionali BNL d'Italia Rome, Italy ATP Tour Masters	Clay	R32	5	Stefanos Tsitsipas (GRE)	3-6 7-5 6-7(4)
05 May 2022	Mutua Madrid Open Madrid, Spain ATP Tour Masters	Clay	R16	5	Stefanos Tsitsipas (GRE)	3-6 4-6
22 Apr 2022	Barcelona Open Banc Sabadell Barcelona, Spain ATP Tour 500	Clay	R16	5	Stefanos Tsitsipas (GRE)	1-6 4-6
25 Oct 2021	Erste Bank Open 500 Vienna, Austria ATP Tour 500	Hard	R32	3	Stefanos Tsitsipas (GRE)	6-7(6) 4-6
29 Oct 2020	Erste Bank Open 500 Vienna, Austria ATP Tour 500	Hard	R16	5	Grigor Dimitrov (BUL)	6-7(5) 6-4 6-3
05 Oct 2020	Roland Garros Paris, France Grand Slam	Clay	R16	6	Stefanos Tsitsipas (GRE)	3-6 6-7(9) 2-6