[19] Grigor Dimitrov 4-6,6-3,2-6 Jannik Sinner [7] 2023-10-02 13:00
Stadium: 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 Beijing | 2023/10/01 11:30 | Holger Rune v Grigor Dimitrov | 3-6,5-7 |
| ATP Beijing | 2023/09/29 04:30 | Mackenzie McDonald v Grigor Dimitrov | 6-2,6-7,1-6 |
| ATP Chengdu | 2023/09/25 11:30 | Alexander Zverev v Grigor Dimitrov | 6-3,7-6 |
| ATP Chengdu | 2023/09/24 11:55 | Grigor Dimitrov v Christopher O'Connell | 6-4,6-1 |
| ATP Chengdu | 2023/09/23 05:00 | Grigor Dimitrov v Juan Pablo Varillas | 6-3,6-4 |
| US Open | 2023/09/02 23:25 | Alexander Zverev v Grigor Dimitrov | 6-7,7-6,6-1,6-1 |
| US Open | 2023/08/31 16:00 | Andy Murray v Grigor Dimitrov | 3-6,4-6,1-6 |
| US Open | 2023/08/29 17:10 | Alex Molcan v Grigor Dimitrov | 7-6,7-6,1-6,5-7,6-7 |
Away History
| ATP Beijing | 2023/10/01 09:35 | Yoshihito Nishioka v Jannik Sinner | 2-6,0-6 |
| ATP Beijing | 2023/09/29 04:30 | Daniel Evans v Jannik Sinner | 4-6,7-6,3-6 |
| US Open | 2023/09/05 00:55 | Alexander Zverev v Jannik Sinner | 6-4,3-6,6-2,4-6,6-3 |
| US Open | 2023/09/02 19:00 | Stan Wawrinka v Jannik Sinner | 3-6,6-2,4-6,2-6 |
| US Open | 2023/08/31 15:00 | Lorenzo Sonego v Jannik Sinner | 4-6,2-6,4-6 |
| US Open | 2023/08/29 23:10 | Yannick Hanfmann v Jannik Sinner | 3-6,1-6,1-6 |
| 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 |