| Challenger Bergamo | 11/03 18:00 | 27 | [91] Jack Draper v Billy Harris [234] | 6-2,6-3 | |
| Challenger Bergamo | 11/02 17:50 | 26 | [91] Jack Draper v Andrea Vavassori [158] | 6-3,6-4 | |
| Challenger Bergamo | 10/31 19:00 | 25 | [91] Jack Draper v Francesco Maestrelli [218] | 6-4,6-4 | |
| ATP Tokyo | 10/17 02:00 | 25 | [13] Alex De Minaur v Jack Draper [88] | 4-6,7-6,7-6 | |
| ATP Tokyo | 10/15 05:00 | 19 | [92] Jack Draper v Jurij Rodionov [100] | 6-1,6-0 | |
| ATP Tokyo | 10/14 02:00 | 14 | [92] Jack Draper v Yuta Shimizu [246] | 6-4,6-4 | |
| Challenger Mouilleron le Captif | 10/06 11:35 | 27 | [92] Jack Draper v Lucas Poullain [282] | 6-7,2-6 | |
| Challenger Mouilleron le Captif | 10/05 12:30 | 26 | [92] Jack Draper v Dino Prizmic [168] | 6-4,3-6,6-3 | |
| Challenger Mouilleron le Captif | 10/04 16:00 | 25 | [106] Jack Draper v Jakub Mensik [152] | 6-4,6-2 | |
| Challenger Orleans | 10/01 14:45 | 29 | [118] Tomas Machac v Jack Draper [106] | 6-4,4-6,6-3 | |
| Challenger Orleans | 09/30 13:40 | 28 | [106] Jack Draper v Luca Van Assche [69] | 7-5,6-3 | |
| Challenger Orleans | 09/29 12:10 | 27 | [106] Jack Draper v Gijs Brouwer [174] | 6-1,6-4 | |
| Challenger Orleans | 09/28 08:30 | 26 | [106] Jack Draper v Tristan Lamasine [356] | 6-4,6-4 | |
| Challenger Orleans | 09/27 10:00 | 25 | [106] Jack Draper v Radu Albot [108] | 6-2,6-2 | |
| Davis Cup | 09/13 12:00 | 1 | [74] Thanasi Kokkinakis v Jack Draper [106] | 7-6,3-6,6-7 | |
| US Open | 09/04 17:40 | 26 | [123] Jack Draper v Andrey Rublev [8] | 3-6,6-3,3-6,4-6 | |
| US Open | 09/02 15:00 | 25 | [89] Michael Mmoh v Jack Draper [123] | 4-6,2-6,6-3,3-6 | |
| US Open | 08/31 15:00 | 24 | [123] Jack Draper v Hubert Hurkacz [17] | 6-2,6-4,7-5 | |
| US Open | 08/29 20:00 | 23 | [102] Radu Albot v Jack Draper [123] | 1-6,4-6,3-6 | |
| ATP Winston-Salem | 08/22 20:10 | 25 | [118] Jack Draper v Tallon Griekspoor [25] | Retired | |
| ATP Winston-Salem | 08/21 18:00 | 24 | [79] Nuno Borges v Jack Draper [118] | 3-6,1-6 | |
| Challenger Winnipeg | 08/17 23:00 | 27 | [123] Jack Draper v Arthur Cazaux [126] | 3-6,3-6 | |
| Challenger Winnipeg | 08/16 18:50 | 26 | [123] Jack Draper v Thai-Son Kwiatkowski [497] | 6-4,7-6 | |
| Challenger Winnipeg | 08/15 23:00 | 25 | [123] Jack Draper v Rio Noguchi [251] | 6-2,6-2 | |
| French Open | 05/29 10:30 | 23 | [55] Jack Draper v Tomas Martin Etcheverry [49] | Retired | |
| ATP Lyon | 05/25 09:00 | 27 | [60] Jack Draper v Francisco Cerundolo [28] | 6-4,4-6,3-6 | |
| ATP Lyon | 05/23 13:00 | 26 | [36] Miomir Kecmanovic v Jack Draper [60] | 4-6,5-7 | |
| ATP Lyon | 05/21 15:45 | 25 | [58] Jack Draper v Alexandre Muller [100] | 6-2,6-3 | |
| ATP Monte Carlo | 04/11 14:55 | 25 | [13] Hubert Hurkacz v Jack Draper [56] | 6-3,6-7,7-5 | |
| ATP Monte Carlo | 04/10 10:30 | 24 | [32] Sebastian Baez v Jack Draper [61] | 3-6,5-7 |