[2] Novak Djokovic 6-3,6-3 Karen Khachanov [17] 2019-11-22 10:50
Stadium: Manolo Santana Stadium Ground: Hardcourt indoor
Head to Head
| 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
| 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 |
| ATP Paris | 2019/11/02 13:00 | Novak Djokovic v Grigor Dimitrov | 7-6,6-4 |
| ATP Paris | 2019/11/01 14:50 | Novak Djokovic v Stefanos Tsitsipas | 6-1,6-2 |
Away History
| 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 |
| ATP Vienna | 2019/10/21 18:40 | Hubert Hurkacz v Karen Khachanov | 4-6,6-7 |
| ATP Moscow | 2019/10/18 13:30 | Andreas Seppi v Karen Khachanov | 3-6,6-3,6-3 |
| ATP Moscow | 2019/10/16 15:50 | Philipp Kohlschreiber v Karen Khachanov | 6-3,3-6,6-7 |
| ATP Shanghai | 2019/10/10 04:30 | Fabio Fognini v Karen Khachanov | 6-3,7-5 |