[42] Jack Draper 4-6,2-6 Karen Khachanov [20] 2023-01-04 00:30
Stadium: Show Court 1 Round: 26 Ground: Hardcourt outdoor
Home History
| ATP Adelaide | 2023/01/02 08:30 | Soonwoo Kwon v Jack Draper | 2-6,1-6 |
| Battle of the Brits | 2022/12/21 20:00 | Andy Murray v Jack Draper | 6-2,1-6,12-10 |
| ATP Next Gen Finals | 2022/11/11 20:00 | Brandon Nakashima v Jack Draper | 4-3,1-4,4-2,4-3 |
| ATP Next Gen Finals | 2022/11/10 19:45 | Lorenzo Musetti v Jack Draper | 1-4,0-4,3-4 |
| ATP Next Gen Finals | 2022/11/09 18:30 | Jack Draper v Chun Hsin Tseng | 1-4,4-2,4-3,4-2 |
| ATP Next Gen Finals | 2022/11/08 21:00 | Jack Draper v Dominic Stephan Stricker | 3-4,3-4,3-4 |
| ATP Paris | 2022/11/02 10:00 | Jack Draper v Frances Tiafoe | 3-6,5-7 |
| ATP Paris | 2022/11/01 11:20 | Arthur Rinderknech v Jack Draper | 3-6,4-6 |
Away History
| ATP Adelaide | 2023/01/03 02:10 | Pedro Cachin v Karen Khachanov | 2-6,4-6 |
| ATP Paris | 2022/11/03 16:05 | Novak Djokovic v Karen Khachanov | 6-4,6-1 |
| ATP Paris | 2022/11/01 20:10 | Karen Khachanov v Marc-Andrea Huesler | 6-3,4-6,6-4 |
| ATP Paris | 2022/10/31 11:50 | Sebastian Baez v Karen Khachanov | 1-6,1-6 |
| ATP Vienna | 2022/10/26 12:35 | Daniel Evans v Karen Khachanov | 6-2,6-2 |
| ATP Vienna | 2022/10/24 12:00 | Karen Khachanov v Jeffrey John Wolf | 7-6,7-5 |
| ATP Antwerp | 2022/10/20 10:30 | Karen Khachanov v Sebastian Korda | 5-7,6-7 |
| ATP Astana | 2022/10/07 12:00 | Karen Khachanov v Novak Djokovic | 4-6,3-6 |