Grigor Dimitrov (Bulgaria) 2 - 3 Alex de Minaur (Australia)

Date	Tournament	Surface	Rd	Opp. Rank	Winner	Score
20 Apr 2023	Barcelona Open Banc Sabadell Barcelona, Spain ATP Tour 500	Clay	R16	19	Alex de Minaur (AUS)	w.o.
17 Feb 2023	ABN Amro Rotterdam, The Netherlands ATP Tour 500	Hard	Q	25	Grigor Dimitrov (BUL)	6-3 3-6 7-6(6)
10 Aug 2022	National Bank Open Toronto/Montreal, Canada ATP Tour Masters	Hard	R32	21	Alex de Minaur (AUS)	6-7(4) 5-7
24 Oct 2020	European Open Antwerp, Belgium ATP Tour 250	Hard	SF	29	Alex de Minaur (AUS)	6-7(4) 7-6(3) 4-6
01 Sep 2019	US Open Flushing Meadows, NY, USA Grand Slam	Hard	R16	38	Grigor Dimitrov (BUL)	7-5 6-3 6-4