[2] Novak Djokovic 7-5,6-3 Karen Khachanov [17] 2019-12-21 13:00
Stadium: Stadium Court Round: 29 Ground: Hardcourt outdoor
Head to Head
| 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 |
| Wimbledon | 2018/07/09 17:50 | Karen Khachanov v Novak Djokovic | 4-6,2-6,2-6 |
Home History
| Mubadala World Tennis Championship | 2019/12/20 13:00 | Novak Djokovic v Stefanos Tsitsipas | 6-3,6-7,4-6 |
| Davis Cup | 2019/11/22 10:50 | Novak Djokovic v Karen Khachanov | 6-3,6-3 |
| Davis Cup | 2019/11/21 12:10 | Benoit Paire v Novak Djokovic | 3-6,3-6 |
| Davis Cup | 2019/11/20 11:40 | Novak Djokovic v Yoshihito Nishioka | 6-1,6-2 |
| ATP World Tour Finals | 2019/11/14 20:00 | Novak Djokovic v Roger Federer | 4-6,3-6 |
| ATP World Tour Finals | 2019/11/12 20:00 | Novak Djokovic v Dominic Thiem | 7-6,3-6,6-7 |
| ATP World Tour Finals | 2019/11/10 14:00 | Novak Djokovic v Matteo Berrettini | 6-2,6-1 |
| ATP Paris | 2019/11/03 14:00 | Novak Djokovic v Denis Shapovalov | 6-3,6-4 |
Away History
| Mubadala World Tennis Championship | 2019/12/20 15:15 | Rafael Nadal v Karen Khachanov | 6-1,6-3 |
| Mubadala World Tennis Championship | 2019/12/19 14:00 | Karen Khachanov v Hyeon Chung | 7-6,6-4 |
| Davis Cup | 2019/11/23 11:25 | Karen Khachanov v Denis Shapovalov | 4-6,6-4,4-6 |
| Davis Cup | 2019/11/22 10:50 | Novak Djokovic v Karen Khachanov | 6-3,6-3 |
| Davis Cup | 2019/11/19 20:05 | Rafael Nadal v Karen Khachanov | 6-3,7-6 |
| Davis Cup | 2019/11/18 16:35 | Borna Coric v Karen Khachanov | 7-6,4-6,4-6 |
| ATP Paris | 2019/10/29 12:05 | Karen Khachanov v Jan-Lennard Struff | 6-7,6-3,5-7 |
| ATP Vienna | 2019/10/25 15:30 | Diego Schwartzman v Karen Khachanov | 7-6,6-2 |