[19] Grigor Dimitrov 4-6,6-3,2-6 Jannik Sinner [7] 2023-08-24 09:00
Stadium: Capital Group Diamond Round: 27 Ground: Hardcourt outdoor
Head to Head
| ATP Miami | 2023/03/26 23:30 | Jannik Sinner v Grigor Dimitrov | 6-3,6-4 |
| ATP Rome | 2020/09/18 09:00 | Grigor Dimitrov v Jannik Sinner | 4-6,6-4,6-4 |
Home History
| ATP Cincinnati | 2023/08/15 17:30 | Alexander Zverev v Grigor Dimitrov | 6-2,6-2 |
| ATP Washington | 2023/08/06 01:20 | Grigor Dimitrov v Daniel Evans | 3-6,6-7 |
| ATP Washington | 2023/08/03 16:00 | Grigor Dimitrov v Emil Ruusuvuori | 6-4,6-3 |
| ATP Washington | 2023/08/01 18:00 | Grigor Dimitrov v Mackenzie McDonald | 7-6,6-2 |
| Wimbledon | 2023/07/10 15:55 | Grigor Dimitrov v Holger Rune | 6-3,6-7,6-7,3-6 |
| Wimbledon | 2023/07/08 17:05 | Frances Tiafoe v Grigor Dimitrov | 2-6,3-6,2-6 |
| Wimbledon | 2023/07/06 17:00 | Ilya Ivashka v Grigor Dimitrov | 3-6,4-6,4-6 |
| Wimbledon | 2023/07/05 11:30 | Sho Shimabukuro v Grigor Dimitrov | 1-6,2-6,1-6 |
Away History
| ATP Cincinnati | 2023/08/16 16:35 | Jannik Sinner v Dusan Lajovic | 4-6,6-7 |
| ATP Toronto | 2023/08/13 20:00 | Jannik Sinner v Alex De Minaur | 6-4,6-1 |
| ATP Toronto | 2023/08/12 23:30 | Tommy Paul v Jannik Sinner | 4-6,4-6 |
| ATP Toronto | 2023/08/12 01:40 | Gael Monfils v Jannik Sinner | 4-6,6-4,3-6 |
| ATP Toronto | 2023/08/09 21:05 | Matteo Berrettini v Jannik Sinner | 4-6,3-6 |
| Wimbledon | 2023/07/14 12:30 | Jannik Sinner v Novak Djokovic | 3-6,4-6,6-7 |
| Wimbledon | 2023/07/11 14:50 | Jannik Sinner v Roman Safiullin | 6-4,3-6,6-2,6-2 |
| Wimbledon | 2023/07/09 13:50 | Jannik Sinner v Daniel Elahi Galan | 7-6,6-4,6-3 |