[2] Jannik Sinner 5-7,6-3,6-3 Karen Khachanov [17] 2023-12-28 20:05
Stadium: Arantxa Sanchez Stadium Round: 26 Ground: Clay
Head to Head
| ATP Miami | 2021/03/28 17:10 | Jannik Sinner v Karen Khachanov | 4-6,7-6,6-4 |
| ATP Great Ocean Road Open | 2021/02/06 05:35 | Jannik Sinner v Karen Khachanov | 7-6,4-6,7-6 |
| US Open | 2020/09/01 15:00 | Jannik Sinner v Karen Khachanov | 6-3,7-6,2-6,0-6,6-7 |
| German Tennis Exhibition | 2020/07/17 09:30 | Jannik Sinner v Karen Khachanov | 6-3,7-6 |
Home History
| Davis Cup | 2023/11/26 17:50 | Alex De Minaur v Jannik Sinner | 3-6,0-6 |
| Davis Cup | 2023/11/25 13:45 | Jannik Sinner v Novak Djokovic | 6-2,2-6,7-5 |
| Davis Cup | 2023/11/23 12:15 | Jannik Sinner v Tallon Griekspoor | 7-6,6-1 |
| ATP World Tour Finals | 2023/11/19 17:00 | Jannik Sinner v Novak Djokovic | 3-6,3-6 |
| ATP World Tour Finals | 2023/11/18 13:30 | Jannik Sinner v Daniil Medvedev | 6-3,6-7,6-1 |
| ATP World Tour Finals | 2023/11/16 20:00 | Jannik Sinner v Holger Rune | 6-2,5-7,6-4 |
| ATP World Tour Finals | 2023/11/14 20:00 | Novak Djokovic v Jannik Sinner | 5-7,7-6,6-7 |
| ATP World Tour Finals | 2023/11/12 13:30 | Jannik Sinner v Stefanos Tsitsipas | 6-4,6-4 |
Away History
| ATP Metz | 2023/11/09 13:00 | Alexander Shevchenko v Karen Khachanov | 6-4,6-4 |
| ATP Metz | 2023/11/07 21:10 | Constant Lestienne v Karen Khachanov | 4-6,4-6 |
| ATP Paris | 2023/11/03 15:00 | Stefanos Tsitsipas v Karen Khachanov | 6-3,6-4 |
| ATP Paris | 2023/11/02 11:35 | Karen Khachanov v Roman Safiullin | 4-6,6-4,6-2 |
| ATP Paris | 2023/10/31 17:35 | Karen Khachanov v Laslo Djere | 6-4,7-5 |
| ATP Paris | 2023/10/30 13:50 | Karen Khachanov v Max Purcell | 6-4,6-4 |
| ATP Vienna | 2023/10/27 12:00 | Daniil Medvedev v Karen Khachanov | 6-3,3-6,6-3 |
| ATP Vienna | 2023/10/25 13:35 | Jiri Lehecka v Karen Khachanov | 3-6,1-6 |