| ATP Montreal | 08/11 02:20 | 25 | [82] Jack Draper v Stefanos Tsitsipas [5] | 7-5,7-6 | |
| ATP Montreal | 08/08 23:40 | 24 | [76] Hugo Gaston v Jack Draper [82] | 2-6,3-6 | |
| ATP Montreal | 08/07 17:20 | 19 | [73] Quentin Halys v Jack Draper [81] | Retired | |
| ATP Montreal | 08/06 20:05 | 14 | Roberto Marcora v Jack Draper | 3-6,0-6 | |
| ATP Washington | 08/02 19:30 | 25 | [8] Andrey Rublev v Jack Draper [81] | 6-4,6-2 | |
| ATP Washington | 08/01 21:20 | 24 | [111] Stefan Kozlov v Jack Draper [81] | 5-7,2-6 | |
| ATP Atlanta | 07/24 16:50 | - | [87] Jack Draper v Ramkumar Ramanathan [196] | 6-7,6-3,6-7 | |
| ATP Atlanta | 07/23 21:30 | 26 | [87] Jack Draper v Christopher Eubanks [153] | 6-4,5-7,6-4 | |
| Wimbledon | 06/30 17:10 | 24 | [27] Alex De Minaur v Jack Draper [94] | 5-7,7-6,6-2,6-3 | |
| Wimbledon | 06/28 14:10 | 23 | [146] Zizou Bergs v Jack Draper [94] | 4-6,4-6,6-7 | |
| ATP Eastbourne | 06/24 13:40 | 28 | [60] Maxime Cressy v Jack Draper [108] | 7-6,6-7,6-3 | |
| ATP Eastbourne | 06/23 12:55 | 27 | [108] Jack Draper v Ryan Peniston [147] | 6-3,6-3 | |
| ATP Eastbourne | 06/22 15:50 | 26 | [15] Diego Schwartzman v Jack Draper [108] | 5-7,6-7 | |
| ATP Eastbourne | 06/20 17:05 | 25 | [34] Jenson Brooksby v Jack Draper [108] | 2-6,2-6 | |
| ATP Queens | 06/15 15:30 | 26 | [99] Jack Draper v Emil Ruusuvuori [56] | 2-6,6-7 | |
| ATP Queens | 06/13 12:30 | 25 | [14] Taylor Fritz v Jack Draper [99] | 3-6,2-6 | |
| Challenger Surbiton | 06/02 11:45 | 26 | [105] Jack Draper v Ryan Peniston [195] | 7-6,5-7,4-6 | |
| Challenger Surbiton | 06/01 18:40 | 25 | [335] Billy Harris v Jack Draper [106] | 2-6,2-6 | |
| ATP Madrid | 05/03 10:00 | 25 | [8] Andrey Rublev v Jack Draper [121] | 2-6,6-4,7-5 | |
| ATP Madrid | 05/01 11:35 | 24 | [27] Lorenzo Sonego v Jack Draper [124] | 4-6,3-6 | |
| Challenger Rome | 04/27 14:35 | 26 | [229] Giulio Zeppieri v Jack Draper [124] | 6-1,6-4 | |
| Challenger Rome | 04/25 13:30 | 25 | [194] Timofey Skatov v Jack Draper [124] | 2-6,1-6 | |
| Challenger St Brieuc | 04/03 13:00 | 29 | [146] Jack Draper v Zizou Bergs [186] | 6-2,5-7,6-4 | |
| Challenger St Brieuc | 04/02 12:30 | 28 | [248] Antoine Escoffier v Jack Draper [146] | 2-6,6-0,0-6 | |
| Challenger St Brieuc | 04/01 14:30 | 27 | [283] Evan Furness v Jack Draper [146] | 2-6,1-6 | |
| Challenger St Brieuc | 03/31 12:10 | 26 | [263] Robin Haase v Jack Draper [146] | 2-6,3-6 | |
| Challenger St Brieuc | 03/30 11:20 | 25 | [252] Illya Marchenko v Jack Draper [146] | 3-6,6-7 | |
| ATP Miami | 03/25 15:00 | 24 | [146] Jack Draper v Cameron Norrie [12] | 6-7,4-6 | |
| ATP Miami | 03/23 16:20 | 23 | [139] Gilles Simon v Jack Draper [146] | 5-7,1-6 | |
| Challenger Forli | 02/27 14:00 | 29 | [274] Alexander Ritschard v Jack Draper [162] | 6-3,3-6,6-7 |