Grigor Dimitrov (Bulgaria) 1 - 5 Jannik Sinner (Italy)

Date Tournament Rnd Winner Score
07 Jul 2025 The Championships UK Wimbledon, Great Britain
ATP Tour Masters, Grass 		R16 Jannik Sinner (ITA Italy) 6-3 7-5 2-2 ret.
04 Jun 2024 Roland Garros FR Paris, France
Grand Slam, Clay 		Q Jannik Sinner (ITA Italy) 2-6 4-6 6-7(3)
31 Mar 2024 Miami Open US Miami, Florida, USA
ATP Tour Masters, Hard 		F Jannik Sinner (ITA Italy) 3-6 1-6
02 Oct 2023 China Open CN Beijing, China
ATP Tour 500, Hard 		Q Jannik Sinner (ITA Italy) 4-6 6-3 2-6
26 Mar 2023 Miami Open US Miami, Florida, USA
ATP Tour Masters, Hard 		R32 Jannik Sinner (ITA Italy) 3-6 4-6
18 Sep 2020 Internazionali BNL d'Italia IT Rome, Italy
ATP Tour Masters, Clay 		R16 Grigor Dimitrov (BUL Bulgaria) 4-6 6-4 6-4