| ATP Indian Wells | 03/15 02:20 | 26 | [2] Carlos Alcaraz v Jack Draper [56] | Retired | |
| ATP Indian Wells | 03/14 01:05 | 25 | [56] Jack Draper v Andy Murray [55] | 7-6,6-2 | |
| ATP Indian Wells | 03/11 19:00 | 24 | [29] Daniel Evans v Jack Draper [56] | 4-6,2-6 | |
| ATP Indian Wells | 03/09 19:00 | 23 | [135] Leandro Riedi v Jack Draper [56] | 1-6,1-6 | |
| Australian Open | 01/16 03:35 | 23 | [2] Rafael Nadal v Jack Draper [38] | 7-5,2-6,6-4,6-1 | |
| ATP Adelaide 2 | 01/13 05:35 | 28 | [40] Jack Draper v Soonwoo Kwon [84] | 6-7,7-6,3-6 | |
| ATP Adelaide 2 | 01/12 00:30 | 27 | [40] Jack Draper v Karen Khachanov [20] | 6-4,7-6 | |
| ATP Adelaide 2 | 01/11 00:30 | 26 | [35] Tommy Paul v Jack Draper [40] | 4-6,4-6 | |
| ATP Adelaide 2 | 01/09 04:35 | 25 | [45] Lorenzo Sonego v Jack Draper [42] | 4-6,2-6 | |
| ATP Adelaide | 01/04 00:30 | 26 | [42] Jack Draper v Karen Khachanov [20] | 4-6,2-6 | |
| ATP Adelaide | 01/02 08:30 | 25 | [83] Soonwoo Kwon v Jack Draper [42] | 2-6,1-6 | |
| Battle of the Brits | 12/21 20:00 | 44 | [49] Andy Murray v Jack Draper [42] | 6-2,1-6,12-10 | |
| ATP Next Gen Finals | 11/11 20:00 | 28 | [49] Brandon Nakashima v Jack Draper [41] | 4-3,1-4,4-2,4-3 | |
| ATP Next Gen Finals | 11/10 19:45 | 3 | [23] Lorenzo Musetti v Jack Draper [41] | 1-4,0-4,3-4 | |
| ATP Next Gen Finals | 11/09 18:30 | 2 | [41] Jack Draper v Chun Hsin Tseng [90] | 1-4,4-2,4-3,4-2 | |
| ATP Next Gen Finals | 11/08 21:00 | 1 | [41] Jack Draper v Dominic Stricker [111] | 3-4,3-4,3-4 | |
| ATP Paris | 11/02 10:00 | 25 | [45] Jack Draper v Frances Tiafoe [21] | 3-6,5-7 | |
| ATP Paris | 11/01 11:20 | 24 | [42] Arthur Rinderknech v Jack Draper [45] | 3-6,4-6 | |
| ATP Basel | 10/24 17:00 | 25 | [1] Carlos Alcaraz v Jack Draper [45] | 3-6,6-2,7-5 | |
| ATP Antwerp | 10/19 18:25 | 26 | [11] Hubert Hurkacz v Jack Draper [48] | 7-6,6-7,6-1 | |
| ATP Antwerp | 10/17 14:55 | 25 | [48] Jack Draper v Jenson Brooksby [41] | 6-1,6-2 | |
| ATP Sofia | 09/27 07:00 | 25 | Jack Draper v Dusan Lajovic | Cancelled | |
| US Open | 09/02 17:45 | 25 | [31] Karen Khachanov v Jack Draper [53] | Retired | |
| US Open | 09/01 00:00 | 24 | [53] Jack Draper v Felix Auger Aliassime [8] | 6-4,6-4,6-4 | |
| US Open | 08/29 22:10 | 23 | [53] Jack Draper v Emil Ruusuvuori [49] | 6-4,6-3,6-3 | |
| ATP Winston-Salem | 08/26 02:15 | 27 | [55] Jack Draper v Marc-Andrea Huesler [102] | 4-6,4-6 | |
| ATP Winston-Salem | 08/25 00:30 | 26 | [231] Dominic Thiem v Jack Draper [55] | 1-6,4-6 | |
| ATP Winston-Salem | 08/23 23:15 | 25 | [61] Fabio Fognini v Jack Draper [55] | 2-6,6-4,1-6 | |
| ATP Montreal | 08/13 01:10 | 27 | [23] Pablo Carreno-Busta v Jack Draper [82] | 7-6,6-1 | |
| ATP Montreal | 08/11 23:00 | 26 | [20] Gael Monfils v Jack Draper [82] | Retired |