| Challenger Las Vegas | 10/20 19:30 | 29 | James Duckworth v Vasek Pospisil | View | |
| Challenger Las Vegas | 10/19 20:35 | 28 | [247] Ernesto Escobedo v James Duckworth [138] | 4-6,6-7 | |
| Challenger Las Vegas | 10/18 18:00 | 27 | Stefan Kozlov v James Duckworth | 2-6,3-6 | |
| Challenger Las Vegas | 10/17 18:00 | 26 | [207] Dmitry Popko v James Duckworth [138] | 3-6,4-6 | |
| Challenger Las Vegas | 10/16 17:30 | 25 | [321] Roy Smith v James Duckworth [138] | 4-6,4-6 | |
| Challenger Fairfield | 10/10 20:10 | 26 | Brandon Nakashima v James Duckworth | 7-6,7-5 | |
| Challenger Fairfield | 10/09 19:00 | 25 | Felix Corwin v James Duckworth | 7-6,5-7,0-6 | |
| ATP Tokyo | 09/29 03:55 | 164 | [143] James Duckworth v Alexei Popyrin [90] | 3-6,6-7 | |
| ATP Tokyo | 09/28 04:30 | 64 | [88] Thomas Fabbiano v James Duckworth [143] | 2-6,3-6 | |
| ATP Chengdu | 09/22 05:00 | 164 | [84] Kamil Majchrzak v James Duckworth [140] | 4-6,7-6,6-4 | |
| ATP Chengdu | 09/21 09:10 | 64 | [317] Harry Bourchier v James Duckworth [140] | 3-6,4-6 | |
| Challenger Jinan | 09/05 06:30 | 26 | [131] James Duckworth v Zhe Li [225] | 6-7,3-6 | |
| Challenger Jinan | 09/04 05:40 | 25 | [131] James Duckworth v Ze Zhang [354] | 6-1,6-4 | |
| Challenger Baotou | 09/01 04:00 | 29 | [131] James Duckworth v Sasi Kumar Mukund [285] | 6-4,6-3 | |
| Challenger Baotou | 08/31 03:00 | 28 | [131] James Duckworth v Frederico Ferreira Silva [282] | 6-3,6-4 | |
| Challenger Baotou | 08/30 03:00 | 27 | [131] James Duckworth v Goncalo Oliveira [265] | Retired | |
| Challenger Baotou | 08/29 04:50 | 26 | [131] James Duckworth v Tsung-Hua Yang [297] | 3-6,7-6,6-1 | |
| Challenger Baotou | 08/28 08:35 | 25 | [131] James Duckworth v Min-Kyu Song [192] | 6-1,6-4 | |
| US Open | 08/20 20:05 | 44 | [205] Marco Trungelliti v James Duckworth [132] | 6-3,5-7,6-3 | |
| Challenger Yokkaichi | 08/11 05:40 | 29 | [164] Yuichi Sugita v James Duckworth [158] | 3-6,6-3,7-6 | |
| Challenger Yokkaichi | 08/10 04:25 | 28 | [143] Tatsuma Ito v James Duckworth [158] | 3-6,4-6 | |
| Challenger Yokkaichi | 08/09 03:00 | 27 | [286] Tung-Lin Wu v James Duckworth [158] | 3-6,1-6 | |
| Challenger Yokkaichi | 08/08 04:05 | 26 | [346] Shintaro Imai v James Duckworth [158] | 2-6,3-6 | |
| Challenger Yokkaichi | 08/07 04:40 | 25 | [468] Lucas Catarina v James Duckworth [158] | 1-6,3-6 | |
| Challenger Chengdu | 08/02 03:00 | 27 | [141] James Duckworth v Yuichi Sugita [197] | 6-3,6-7,4-6 | |
| Challenger Chengdu | 08/01 04:55 | 26 | [141] James Duckworth v Thomas Fancutt [366] | 6-2,6-2 | |
| Challenger Chengdu | 07/31 02:00 | 25 | [141] James Duckworth v Runhao Hua [404] | 6-7,7-6,6-3 | |
| Wimbledon | 06/26 12:25 | 45 | [147] James Duckworth v Viktor Galovic [199] | 6-3,3-6,9-11 | |
| Wimbledon | 06/24 10:00 | 44 | [147] James Duckworth v Jan Choinski [284] | 6-1,7-5 | |
| Challenger Ilkley | 06/18 15:20 | 25 | [151] James Duckworth v Gregoire Barrere [115] | 6-7,3-6 |