| Challenger Nur-Sultan | 03/05 05:00 | 27 | [102] James Duckworth v Prajnesh Gunneswaran [134] | 4-6,6-2,6-7 | |
| Challenger Nur-Sultan | 03/04 05:00 | 26 | [102] James Duckworth v Vladyslav Manafov [253] | 6-2,6-7,7-5 | |
| Challenger Nur-Sultan | 03/03 06:05 | 25 | James Duckworth v Alibek Kachmazov | 6-4,5-7,7-5 | |
| ATP Singapore | 02/23 10:00 | 25 | [100] James Duckworth v Yannick Hanfmann [105] | 2-6,4-6 | |
| Australian Open | 02/10 01:30 | 24 | [105] James Duckworth v Felix Auger Aliassime [19] | 4-6,1-6,2-6 | |
| Australian Open | 02/08 04:45 | 23 | [120] Damir Dzumhur v James Duckworth [105] | 3-6,2-6,4-6 | |
| ATP Murray River Open | 02/05 01:25 | 26 | [105] James Duckworth v Corentin Moutet [80] | 6-7,4-6 | |
| ATP Murray River Open | 02/03 03:30 | 25 | [32] Ugo Humbert v James Duckworth [105] | 6-7,4-6 | |
| ATP Murray River Open | 02/02 02:35 | 24 | [105] James Duckworth v Tomas Machac [197] | 6-3,6-4 | |
| ATP Nur-Sultan | 10/26 12:45 | 25 | [61] Fernando Verdasco v James Duckworth [97] | 6-4,7-6 | |
| ATP Köln 2 | 10/20 16:05 | 25 | [46] Jannik Sinner v James Duckworth [97] | 6-1,6-2 | |
| ATP Köln 2 | 10/18 10:30 | 164 | [93] James Duckworth v Dennis Novak [94] | 4-6,5-7 |