Grigor Dimitrov (Bulgaria) 1 - 5 Kei Nishikori (Japan)

Date	Tournament	Surface	Rd	Opp. Rank	Winner	Score
03 Jan 2019	Brisbane International Brisbane, Australia ATP Tour 250	Hard	Q	9	Kei Nishikori (JPN)	5-7 5-7
15 May 2018	Internazionali BNL d'Italia Rome, Italy ATP Tour Masters	Clay	R32	24	Kei Nishikori (JPN)	7-6(4) 5-7 4-6
08 Jan 2017	Brisbane International Brisbane, Australia ATP Tour 250	Hard	F	5	Grigor Dimitrov (BUL)	6-2 2-6 6-3
29 Jul 2016	National Bank Open Toronto/Montreal, Canada ATP Tour Masters	Hard	Q	6	Kei Nishikori (JPN)	3-6 6-3 2-6
23 Mar 2014	Miami Open Miami, Florida, USA ATP Tour Masters	Hard	R32	21	Kei Nishikori (JPN)	6-7(1) 5-7
08 Oct 2013	Shanghai Rolex Masters Shanghai, China ATP Tour Masters	Hard	R64	18	Kei Nishikori (JPN)	3-6 4-6