| ATP Madrid | 04/24 14:40 | 23 | [93] Thanasi Kokkinakis v Jack Draper [43] | 3-6,6-3,5-7 | |
| ATP Munich | 04/19 09:00 | 27 | [15] Taylor Fritz v Jack Draper [46] | 4-6,6-3,7-6 | |
| ATP Munich | 04/17 09:00 | 26 | [179] Rudolf Molleker v Jack Draper [46] | 6-4,1-6,1-6 | |
| ATP Munich | 04/15 12:30 | 25 | [119] Vit Kopriva v Jack Draper [46] | 1-6,7-5,4-6 | |
| ATP Monte Carlo | 04/09 12:35 | 24 | [8] Hubert Hurkacz v Jack Draper [39] | 6-4,3-6,7-6 | |
| ATP Miami | 03/23 18:00 | 24 | [23] Nicolas Jarry v Jack Draper [42] | 7-6,4-6,7-6 | |
| ATP Miami | 03/20 16:55 | 23 | [42] Jack Draper v Taro Daniel [78] | 6-3,6-2 | |
| ATP Indian Wells | 03/06 19:00 | 23 | [66] Christopher O'Connell v Jack Draper [37] | 1-6,6-3,6-2 | |
| ATP Acapulco | 03/02 01:00 | 28 | [50] Jack Draper v Alex De Minaur [9] | Retired | |
| ATP Acapulco | 03/01 00:00 | 27 | [53] Miomir Kecmanovic v Jack Draper [50] | 2-6,2-6 | |
| ATP Acapulco | 02/29 00:00 | 26 | [82] Yoshihito Nishioka v Jack Draper [50] | 3-6,0-6 | |
| ATP Acapulco | 02/27 00:00 | 25 | [51] Jack Draper v Tommy Paul [14] | 6-0,6-4 | |
| ATP Los Cabos | 02/20 03:50 | 25 | [79] Thanasi Kokkinakis v Jack Draper [51] | 4-6,7-6,6-4 | |
| Australian Open | 01/18 04:20 | 24 | [14] Tommy Paul v Jack Draper [55] | 6-2,3-6,6-3,7-5 | |
| Australian Open | 01/16 03:10 | 23 | [66] Marcos Giron v Jack Draper [55] | 4-6,6-3,6-4,0-6,2-6 | |
| ATP Adelaide | 01/13 05:30 | 29 | [62] Jack Draper v Jiri Lehecka [32] | 6-4,4-6,3-6 | |
| ATP Adelaide | 01/12 08:00 | 28 | [62] Jack Draper v Alexander Bublik [31] | 7-6,6-4 | |
| ATP Adelaide | 01/11 08:00 | 27 | [14] Tommy Paul v Jack Draper [62] | 1-6,4-6 | |
| ATP Adelaide | 01/10 02:00 | 26 | [55] Miomir Kecmanovic v Jack Draper [62] | 7-5,6-7,6-7 | |
| ATP Adelaide | 01/08 05:35 | 25 | Jack Draper v Sebastian Baez | 6-1,6-3 | |
| ATP Adelaide | 01/07 02:10 | 14 | Jack Draper v James McCabe | Cancelled | |
| Davis Cup | 11/23 17:10 | 27 | [55] Miomir Kecmanovic v Jack Draper [60] | 7-6,7-6 | |
| ATP Sofia | 11/11 13:00 | 29 | [82] Jack Draper v Adrian Mannarino [25] | 6-7,6-2,3-6 | |
| ATP Sofia | 11/10 14:00 | 28 | [82] Jack Draper v Jan-Lennard Struff [28] | 6-3,6-4 | |
| ATP Sofia | 11/09 13:15 | 27 | [82] Jack Draper v Cem Ilkel [259] | 6-2,6-2 | |
| ATP Sofia | 11/08 17:05 | 26 | [27] Lorenzo Musetti v Jack Draper [82] | 5-7,2-6 | |
| ATP Sofia | 11/07 20:35 | 25 | [82] Jack Draper v Maximilian Marterer [97] | 6-3,6-2 | |
| Challenger Bergamo | 11/05 15:35 | 29 | [91] Jack Draper v David Goffin [110] | 1-6,7-6,6-3 | |
| Challenger Bergamo | 11/04 15:30 | 28 | [91] Jack Draper v Brandon Nakashima [151] | 6-1,3-6,7-5 | |
| Challenger Bergamo | 11/03 18:00 | 27 | [91] Jack Draper v Billy Harris [234] | 6-2,6-3 |