[18] Karen Khachanov 4-6,3-6 Novak Djokovic [7] 2022-10-07 12:00
Stadium: Center Court Round: 27 Ground: Hardcourt indoor
Head to Head
| ATP Belgrade | 2022/04/23 12:00 | Novak Djokovic v Karen Khachanov | 4-6,6-1,6-2 |
| ATP Dubai | 2022/02/23 15:00 | Novak Djokovic v Karen Khachanov | 6-3,7-6 |
| French Open | 2020/10/05 13:30 | Novak Djokovic v Karen Khachanov | 6-4,6-3,6-3 |
| ATP Dubai | 2020/02/27 16:15 | Novak Djokovic v Karen Khachanov | 6-2,6-2 |
| Mubadala World Tennis Championship | 2019/12/21 13:00 | Novak Djokovic v Karen Khachanov | 7-5,6-3 |
| Davis Cup | 2019/11/22 10:50 | Novak Djokovic v Karen Khachanov | 6-3,6-3 |
| Mubadala World Tennis Championship | 2018/12/28 15:00 | Karen Khachanov v Novak Djokovic | 4-6,2-6 |
| ATP Paris | 2018/11/04 14:00 | Karen Khachanov v Novak Djokovic | 7-5,6-4 |
Home History
| ATP Astana | 2022/10/06 06:00 | Marin Cilic v Karen Khachanov | 6-2,3-6,3-6 |
| ATP Nur-Sultan | 2022/10/04 05:00 | Maxime Cressy v Karen Khachanov | 4-6,6-7 |
| US Open | 2022/09/09 19:00 | Karen Khachanov v Casper Ruud | 6-7,2-6,7-5,2-6 |
| US Open | 2022/09/07 01:05 | Nick Kyrgios v Karen Khachanov | 5-7,6-4,5-7,7-6,4-6 |
| US Open | 2022/09/04 20:50 | Pablo Carreno Busta v Karen Khachanov | 6-4,3-6,1-6,6-4,3-6 |
| US Open | 2022/08/31 23:10 | Karen Khachanov v Thiago Monteiro | 6-3,6-3,5-7,6-4 |
| US Open | 2022/08/29 18:45 | Karen Khachanov v Denis Kudla | 3-6,6-1,6-2,6-2 |
| ATP Cincinnati | 2022/08/15 22:40 | Karen Khachanov v Sebastian Korda | 3-6,4-6 |
Away History
| ATP Astana | 2022/10/06 12:00 | Botic Van De Zandschulp v Novak Djokovic | 3-6,1-6 |
| ATP Astana | 2022/10/05 12:00 | Cristian Garin v Novak Djokovic | 1-6,1-6 |
| ATP Tel Aviv | 2022/10/02 15:30 | Novak Djokovic v Marin Cilic | 6-3,6-4 |
| ATP Tel Aviv | 2022/10/01 16:30 | Novak Djokovic v Roman Safiullin | 6-1,7-6 |
| ATP Tel Aviv | 2022/09/30 13:10 | Novak Djokovic v Vasek Pospisil | 7-6,6-3 |
| ATP Tel Aviv | 2022/09/29 16:35 | Novak Djokovic v Pablo Andujar | 6-0,6-3 |
| Laver Cup | 2022/09/25 13:00 | Novak Djokovic v Felix Auger Aliassime | 3-6,6-7 |
| Laver Cup | 2022/09/24 18:00 | Novak Djokovic v Frances Tiafoe | 6-1,6-3 |