Grigor Dimitrov (Bulgaria) 2 - 5 Daniil Medvedev (___)

Date	Tournament	Surface	Rd	Opp. Rank	Winner	Score
18 Feb 2023	ABN Amro Rotterdam, The Netherlands ATP Tour 500	Hard	SF	11	Daniil Medvedev (___)	1-6 2-6
29 Oct 2022	Erste Bank Open 500 Vienna, Austria ATP Tour 500	Hard	SF	4	Daniil Medvedev (___)	4-6 2-6
13 Oct 2021	BNP Paribas Open Indian Wells, CA, USA ATP Tour Masters	Hard	R16	2	Grigor Dimitrov (BUL)	4-6 6-4 6-3
19 Aug 2021	W & S Open Cincinnati, OH, USA ATP Tour Masters	Hard	R16	2	Daniil Medvedev (___)	3-6 3-6
06 Sep 2019	US Open Flushing Meadows, NY, USA Grand Slam	Hard	SF	5	Daniil Medvedev (___)	6-7(5) 4-6 3-6
03 Aug 2017	Mubadala Citi DC Open Washington, DC, USA ATP Tour 500	Hard	R16	50	Daniil Medvedev (___)	4-6 2-6
23 Jun 2017	cinch Championships London / Queen`s Club, Great Britain ATP Tour 500	Grass	Q	60	Grigor Dimitrov (BUL)	6-3 3-6 6-3