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

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