[52] James Duckworth 6-3,3-6,1-6 Karen Khachanov [31] 2021-10-20 18:10
Estádio: Central Court Round: 26 Ground: Hardcourt indoor
Head to Head
| Jogos Olímpicos 2020 - Masculino | 2021/07/27 06:20 | James Duckworth v Karen Khachanov | 5-7,1-6 |
| ATP - São Peterburgo | 2020/10/13 14:00 | Karen Khachanov v James Duckworth | 6-4,6-4 |
Home History
| ATP - Moscovo | 2021/10/18 18:50 | James Duckworth v Borna Gojo | 3-6,7-5,6-2 |
| ATP - Indian Wells | 2021/10/07 19:45 | Mackenzie McDonald v James Duckworth | 6-3,6-3 |
| ATP - Sófia | 2021/10/01 15:00 | Jannik Sinner v James Duckworth | 7-6,6-4 |
| ATP - Sófia | 2021/09/30 11:20 | James Duckworth v Benoit Paire | 6-4,6-4 |
| ATP - Sófia | 2021/09/29 09:00 | Emil Ruusuvuori v James Duckworth | 6-3,4-6,4-6 |
| ATP - Nur-Sultã | 2021/09/26 08:30 | James Duckworth v Soonwoo Kwon | 6-7,3-6 |
| ATP - Nur-Sultã | 2021/09/25 08:00 | Ilya Ivashka v James Duckworth | 3-6,6-7 |
| ATP - Nur-Sultã | 2021/09/24 09:10 | James Duckworth v John Millman | 6-4,6-4 |
Away History
| ATP - Indian Wells | 2021/10/13 21:25 | Nikoloz Basilashvili v Karen Khachanov | 6-4,7-6 |
| ATP - Indian Wells | 2021/10/12 19:40 | Karen Khachanov v Pablo Carreno Busta | 6-0,6-4 |
| ATP - Indian Wells | 2021/10/11 01:00 | Karen Khachanov v Emil Ruusuvuori | 6-2,7-5 |
| ATP - Metz | 2021/09/23 12:00 | Peter Gojowczyk v Karen Khachanov | 6-3,7-6 |
| ATP - Metz | 2021/09/21 11:30 | Alexandre Muller v Karen Khachanov | 6-4,1-6,3-6 |
| Open dos EUA | 2021/08/31 15:00 | Karen Khachanov v Lloyd Harris | 4-6,6-1,6-4,3-6,2-6 |
| ATP - Cincinnati | 2021/08/18 14:00 | Karen Khachanov v Felix Auger Aliassime | 7-6,3-6,4-6 |
| ATP - Cincinnati | 2021/08/17 01:25 | Kevin Anderson v Karen Khachanov | 2-6,4-6 |