Grigor Dimitrov (Bulgaria) 6 - 2 Milos Raonic (Canada)

Date	Tournament	Surface	Rd	Opp. Rank	Winner	Score
23 Oct 2020	European Open Antwerp, Belgium ATP Tour 250	Hard	Q	19	Grigor Dimitrov (BUL)	wo
09 May 2018	Mutua Madrid Open Madrid, Spain ATP Tour Masters	Clay	R32	24	Milos Raonic (CAN)	5-7 6-3 3-6
07 Jan 2017	Brisbane International Brisbane, Australia ATP Tour 250	Hard	SF	3	Grigor Dimitrov (BUL)	7-6(7) 6-2
08 Oct 2016	China Open Beijing, China ATP Tour 500	Hard	SF	6	Grigor Dimitrov (BUL)	wo
18 Jan 2014	Australian Open Melbourne, Australia Grand Slam	Hard	R32	11	Grigor Dimitrov (BUL)	6-3 3-6 6-4 7-6(10)
03 Jan 2013	Brisbane International Brisbane, Australia ATP Tour 250	Hard	R16	13	Grigor Dimitrov (BUL)	6-3 6-4
21 Oct 2011	Stockholm Open Stockholm, Sweden ATP Tour 250	Hard	Q	29	Milos Raonic (CAN)	5-7 4-6
19 Jan 2009	USA Futures 2 Hollywood, FL, USA Futures	Clay	R32	914	Grigor Dimitrov (BUL)	6-4 6-2