Grigor Dimitrov (Bulgaria) 1 - 7 Roger Federer (Switzerland)

Date	Tournament	Surface	Rd	Opp. Rank	Winner	Score
03 Sep 2019	US Open Flushing Meadows, NY, USA Grand Slam	Hard	Q	3	Grigor Dimitrov (BUL)	3-6 6-4 3-6 6-4 6-2
18 Feb 2018	ABN Amro Rotterdam, The Netherlands ATP Tour 500	Hard	F	2	Roger Federer (SUI)	2-6 2-6
10 Jul 2017	The Championships Wimbledon, Great Britain Grand Slam	Grass	R16	5	Roger Federer (SUI)	4-6 2-6 4-6
22 Jan 2016	Australian Open Melbourne, Australia Grand Slam	Hard	R32	3	Roger Federer (SUI)	4-6 6-3 1-6 4-6
08 Jan 2016	Brisbane International Brisbane, Australia ATP Tour 250	Hard	Q	3	Roger Federer (SUI)	4-6 7-6(4) 4-6
10 Jan 2015	Brisbane International Brisbane, Australia ATP Tour 250	Hard	SF	2	Roger Federer (SUI)	2-6 2-6
24 Oct 2014	Swiss Indoors Basel, Switzerland ATP Tour 500	Hard	Q	2	Roger Federer (SUI)	6-7(4) 2-6
25 Oct 2013	Swiss Indoors Basel, Switzerland ATP Tour 500	Hard	Q	6	Roger Federer (SUI)	3-6 6-7(2)