[17] Karen Khachanov 4-6,6-4,4-6 Denis Shapovalov [15] 2019-11-23 11:25
Stadium: Manolo Santana Stadium Round: 28
Home History
| 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 |
| 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 |
Away History
| Davis Cup | 2019/11/21 18:55 | Alex De Minaur v Denis Shapovalov | 3-6,6-3,7-5 |
| Davis Cup | 2019/11/19 19:10 | Taylor Fritz v Denis Shapovalov | 6-7,3-6 |
| Davis Cup | 2019/11/18 17:20 | Matteo Berrettini v Denis Shapovalov | 6-7,7-6,6-7 |
| ATP Paris | 2019/11/03 14:00 | Novak Djokovic v Denis Shapovalov | 6-3,6-4 |
| ATP Paris | 2019/11/01 18:30 | Denis Shapovalov v Gael Monfils | 6-2,6-2 |
| ATP Paris | 2019/10/31 16:00 | Alexander Zverev v Denis Shapovalov | 2-6,7-5,2-6 |
| ATP Paris | 2019/10/30 11:30 | Denis Shapovalov v Fabio Fognini | 3-6,6-3,6-3 |
| ATP Vienna | 2019/10/23 10:00 | Pablo Carreno Busta v Denis Shapovalov | 6-3,7-5 |