[3] Daniil Medvedev 6-7,6-4,3-6 Jannik Sinner [4] 2023-10-29 13:00
Stadium: Center Court Round: 29 Ground: Hardcourt indoor
Head to Head
| ATP Beijing | 2023/10/04 11:30 | Jannik Sinner v Daniil Medvedev | 7-6,7-6 |
| ATP Miami | 2023/04/02 17:00 | Jannik Sinner v Daniil Medvedev | 5-7,3-6 |
| ATP Rotterdam | 2023/02/19 14:30 | Jannik Sinner v Daniil Medvedev | 7-5,2-6,2-6 |
| ATP Vienna | 2022/10/28 14:15 | Daniil Medvedev v Jannik Sinner | 6-4,6-2 |
| ATP World Tour Finals | 2021/11/18 20:00 | Daniil Medvedev v Jannik Sinner | 6-0,6-7,7-6 |
| ATP Marseille | 2021/03/12 15:40 | Daniil Medvedev v Jannik Sinner | 6-2,6-4 |
| ATP Marseille | 2020/02/20 15:25 | Daniil Medvedev v Jannik Sinner | 1-6,6-1,6-2 |
Home History
| ATP Vienna | 2023/10/28 12:00 | Daniil Medvedev v Stefanos Tsitsipas | 6-4,7-6 |
| ATP Vienna | 2023/10/27 12:00 | Daniil Medvedev v Karen Khachanov | 6-3,3-6,6-3 |
| ATP Vienna | 2023/10/26 12:00 | Daniil Medvedev v Grigor Dimitrov | 3-6,6-2,6-4 |
| ATP Vienna | 2023/10/25 13:45 | Daniil Medvedev v Arthur Fils | 6-4,6-2 |
| ATP Shanghai | 2023/10/08 06:00 | Sebastian Korda v Daniil Medvedev | 7-6,6-2 |
| ATP Shanghai | 2023/10/07 06:25 | Cristian Garin v Daniil Medvedev | 3-6,3-6 |
| ATP Beijing | 2023/10/04 11:30 | Jannik Sinner v Daniil Medvedev | 7-6,7-6 |
| ATP Beijing | 2023/10/03 10:45 | Alexander Zverev v Daniil Medvedev | 4-6,3-6 |
Away History
| ATP Vienna | 2023/10/28 14:30 | Andrey Rublev v Jannik Sinner | 5-7,6-7 |
| ATP Vienna | 2023/10/27 19:40 | Frances Tiafoe v Jannik Sinner | 3-6,4-6 |
| ATP Vienna | 2023/10/26 16:45 | Lorenzo Sonego v Jannik Sinner | 2-6,4-6 |
| ATP Vienna | 2023/10/25 15:30 | Ben Shelton v Jannik Sinner | 6-7,5-7 |
| ATP Shanghai | 2023/10/10 10:30 | Jannik Sinner v Ben Shelton | 6-2,3-6,6-7 |
| ATP Shanghai | 2023/10/08 10:30 | Jannik Sinner v Sebastian Baez | 3-6,6-3,6-2 |
| ATP Shanghai | 2023/10/07 08:05 | Jannik Sinner v Marcos Giron | 7-6,6-2 |
| ATP Beijing | 2023/10/04 11:30 | Jannik Sinner v Daniil Medvedev | 7-6,7-6 |