Grigor Dimitrov (Bulgaria) 1 - 3 Mikhail Kukushkin (Kazakhstan)

Date	Tournament	Surface	Rd	Opp. Rank	Winner	Score
24 Oct 2018	Erste Bank Open 500 Vienna, Austria ATP Tour 500	Hard	R32	71	Mikhail Kukushkin (KAZ)	`4-6 6-4 4-6
02 Sep 2015	US Open Flushing Meadows, NY, USA Grand Slam	Hard	R64	56	Mikhail Kukushkin (KAZ)	3-6 6-7(2) 6-2 6-4 4-6
16 Apr 2012	Monte-Carlo Rolex Masters Monte-Carlo, Monaco ATP Tour Masters	Clay	Q-R16	70	Mikhail Kukushkin (KAZ)	4-6 5-7
21 Mar 2012	Miami Open Miami, Florida, USA ATP Tour Masters	Hard	R128	72	Grigor Dimitrov (BUL)	6-2 6-2