| ATP - Montreal | 08/06 16:20 | 14 | James Duckworth v Gabriel Diallo | 3-6,6-7 | |
| ATP - Washington | 08/01 18:35 | 24 | [59] James Duckworth v Borna Gojo [198] | 6-4,6-7,2-6 | |
| ATP - Atlanta | 07/28 23:00 | 26 | [30] Alex De Minaur v James Duckworth [62] | 6-4,6-4 | |
| ATP - Atlanta | 07/26 23:35 | 25 | [141] Dominik Koepfer v James Duckworth [62] | 1-6,7-6,3-6 | |
| ATP - Newport | 07/15 18:40 | 27 | [102] Jason Kubler v James Duckworth [74] | 7-5,7-6 | |
| ATP - Newport | 07/13 15:00 | 26 | [86] Quentin Halys v James Duckworth [74] | 5-7,6-3,2-6 | |
| ATP - Newport | 07/12 16:40 | 25 | [140] Liam Broady v James Duckworth [74] | 2-6,6-4,2-6 | |
| Challenger - Porto | 07/09 10:00 | 28 | [74] James Duckworth v Altug Celikbilek [179] | 6-7,4-6 | |
| Challenger - Porto | 07/08 10:50 | 27 | [74] James Duckworth v Aidan Mchugh [356] | 7-6,6-0 | |
| Challenger - Porto | 07/06 10:40 | 26 | [74] James Duckworth v Antoine Bellier [217] | 6-2,6-1 | |
| Challenger - Porto | 07/04 13:15 | 25 | James Duckworth v Pedro Araujo | 6-3,6-4 | |
| Wimbledon | 06/27 17:30 | 23 | [52] Andy Murray v James Duckworth [74] | 4-6,6-3,6-2,6-4 |