Grigor Dimitrov (Bulgaria) 5 - 2 Jan-Lennard Struff (Germany)

Date	Tournament	Surface	Rd	Opp. Rank	Winner	Score
24 Mar 2023	Miami Open Miami, Florida, USA ATP Tour Masters	Hard	R64	103	Grigor Dimitrov (BUL)	4-6 7-6(5) 6-4
12 Apr 2021	Monte-Carlo Rolex Masters Monte-Carlo, Monaco ATP Tour Masters	Clay	R64	41	Grigor Dimitrov (BUL)	6-3 6-4
13 May 2019	Internazionali BNL d'Italia Rome, Italy ATP Tour Masters	Clay	R64	49	Jan-Lennard Struff (GER)	4-6 7-6(5) 3-6
17 Apr 2019	Monte-Carlo Rolex Masters Monte-Carlo, Monaco ATP Tour Masters	Clay	R32	44	Grigor Dimitrov (BUL)	7-6(2) 6-4
19 Apr 2017	Monte-Carlo Rolex Masters Monte-Carlo, Monaco ATP Tour Masters	Clay	R32	58	Jan-Lennard Struff (GER)	6-4 3-6 2-6
17 Oct 2013	Stockholm Open Stockholm, Sweden ATP Tour 250	Hard	R16	117	Grigor Dimitrov (BUL)	6-1 6-3
01 Aug 2010	Apano Cup Dortmund, Germany Futures	Clay	F	486	Grigor Dimitrov (BUL)	7-5 7-5