Grigor Dimitrov (Bulgaria) 3 - 1 Mackenzie McDonald (USA)

Date	Tournament	Surface	Rd	Opp. Rank	Winner	Score
29 Sep 2023	China Open Beijing, China ATP Tour 500	Hard	R32	39	Grigor Dimitrov (BUL)	2-6 7-6(4) 6-1
02 Aug 2023	Mubadala Citi DC Open Washington, DC, USA ATP Tour 500	Hard	R32	60	Grigor Dimitrov (BUL)	7-6(6) 6-2
24 Mar 2022	Miami Open Miami, Florida, USA ATP Tour Masters	Hard	R64	54	Mackenzie McDonald (USA)	1-6 4-6
17 Jan 2018	Australian Open Melbourne, Australia Grand Slam	Hard	R64	178	Grigor Dimitrov (BUL)	4-6 6-2 6-4 0-6 8-6