| ATP - Nur-Sultan | 10/26 12:45 | 25 | [61] Fernando Verdasco v James Duckworth [97] | 6-4,7-6 | |
| ATP - Keulen 2 | 10/20 16:05 | 25 | [46] Jannik Sinner v James Duckworth [97] | 6-1,6-2 | |
| ATP - Keulen 2 | 10/18 10:30 | 164 | [93] James Duckworth v Dennis Novak [94] | 4-6,5-7 | |
| ATP - Keulen 2 | 10/17 09:00 | 64 | [93] James Duckworth v Mischa Zverev [268] | 6-3,5-7,6-2 | |
| ATP - St Petersburg | 10/13 14:00 | 25 | [17] Karen Khachanov v James Duckworth [93] | 6-4,6-4 | |
| French Open | 09/28 12:25 | 23 | [58] Tommy Paul v James Duckworth [91] | 6-2,6-3,6-2 | |
| ATP - Rome | 09/13 08:00 | 19 | [134] Facundo Bagnis v James Duckworth [84] | 7-6,6-1 | |
| ATP - Rome | 09/12 08:00 | 14 | [84] James Duckworth v Yasutaka Uchiyama [86] | Retired | |
| ATP - Kitzbühel | 09/07 12:20 | 45 | Jurij Rodionov v James Duckworth | Cancelled | |
| US Open | 09/02 00:55 | 23 | [100] Salvatore Caruso v James Duckworth [84] | 4-6,7-5,7-5,6-2 | |
| UTR Pro Tennis Series - Brisbane | 08/18 02:30 | - | James Duckworth v Alexander Crnokrak | View | |
| UTR Pro Tennis Series - Brisbane | 08/17 02:30 | - | James Duckworth v Dane Sweeny | 6-3,6-2 |