Grigor Dimitrov (Bulgaria) 2 - 2 Denis Shapovalov (Canada)

Date	Tournament	Rnd	Winner	Score
15 Aug 2022	W & S Open Cincinnati, OH, USA ATP Tour Masters, Hard	R64	Denis Shapovalov (CAN )	6-7(4) 3-6
19 Sep 2020	Internazionali BNL d'Italia Rome, Italy ATP Tour Masters, Clay	Q	Denis Shapovalov (CAN )	2-6 6-3 2-6
10 Feb 2020	ABN Amro Rotterdam, The Netherlands ATP Tour 500, Hard	R32	Grigor Dimitrov (BUL )	6-3 7-6(3)
27 Jul 2016	National Bank Open Toronto/Montreal, Canada ATP Tour Masters, Hard	R32	Grigor Dimitrov (BUL )	6-4 6-3