| 2020-09-02 19:45:4002/09/20 | Crook Town v Yorkshire Amateur | 1 - 1 | | 2020-21 | The Sir Tom Cowie Millfield | FA CupExtra Preliminary Round Qualifying | 219 |
| Daniel Kent (50) |
| Roy Fogarty (68) |
| 2020-09-05 15:00:0005/09/20 | Crook Town v Redcar Athletic | 3 - 0 | Division 2 | 2020-21 | The Sir Tom Cowie Millfield | | 227 |
| Christian Holliday (15, 29) Daniel Kent (68) |
| 2020-09-09 19:30:0009/09/20 | Crook Town v Newcastle University | 1 - 2 | Division 2 | 2020-21 | The Sir Tom Cowie Millfield | | 225 |
| Daniel Kent (13) |
| Stephen Pennington (54) Niza Chilufya (60 pen) |
| 2020-09-12 15:00:5712/09/20 | Crook Town v Marske United | 0 - 2 | | 2020-21 | The Sir Tom Cowie Millfield | FA CupPreliminary Round Qualifying | 300 |
| Craig Gott (67 pen) Kevin Burgess (80), Gott missed pen (67) |
| 2020-09-16 19:30:0016/09/20 | West Allotment Celtic v Crook Town | 0 - 3 | Division 2 | 2020-21 | Sam Smith's Park | | 86 |
| Abubaker Salim missed pen (1), Michael Trodd sent off (79) |
| Christian Holliday (8) Dale Elgie (22) Joe Hillerby (43) |
| 2020-09-19 15:00:2019/09/20 | Crook Town v Albion Sports | 1 - 0 | | 2020-21 | The Sir Tom Cowie Millfield | FA VaseFirst Round Qualifying | 208 |
| Jamie Tumilty (80) |
| 2020-09-23 19:30:0023/09/20 | Crook Town v Durham City | 5 - 1 | Division 2 | 2020-21 | The Sir Tom Cowie Millfield | | 158 |
| Jamie Tumilty (5) Tom Gavin (36) Daniel Kent 2 (46, 70) Joe Hillerby (51) |
| Harry Stansfield (48) |
| 2020-09-26 15:00:0026/09/20 | Crook Town v Billingham Synthonia | 2 - 2 | Division 2 | 2020-21 | The Sir Tom Cowie Millfield | | 150 |
| Matthew Crossen (73) Jamie Tumilty (88) |
| Daniel Chapman (27 pen) Ian Ward (65), Chapman sent off (91) |
| 2020-09-30 19:30:0030/09/20 | Crook Town v Jarrow | 4 - 0 | Division 2 | 2020-21 | The Sir Tom Cowie Millfield | | 150 |
| Corey Nicholson (43) Daniel Kent 3 (43, 47, 63 pen) |
| Nicholas Little sent off (63) Alexander Bone sent off (82) |
| 2020-10-03 15:00:0003/10/20 | Washington v Crook Town | 2 - 3 | Division 2 | 2020-21 | Ford Hub Sports Complex | | 69 |
| Lewis McGeoch (20 pen) Ethan Barella (36) |
| Matthew Crossen (49) Jamie Tumilty (70) Christian Holliday (90) |
| 2020-10-06 19:30:0006/10/20 | Tow Law Town v Crook Town | 4 - 3 | Division 2 | 2020-21 | Ironworks Road | | 150 |
| Barrie Smith (1 pen, 60) Thomas McAloon (12) Michael Brown (23) |
| Daniel Kent 3 (25, 82, 89), Jeffery Smith sent off (60) Dale Elgie sent off (80) |
| 2020-10-10 15:00:0210/10/20 | Holker Old Boys v Crook Town | 2 - 1 | | 2020-21 | | FA VaseSecond Qualifying Round | |
| 2020-10-14 19:30:0014/10/20 | Ryton & Crawcrook Albion v Crook Town | 2 - 5 | Division 2 | 2020-21 | Kingsley Park | | 119 |
| Callum Turnbull (2 pen) Matthew Slee (73) |
| Jamie Tumilty 2 (34, 70) Daniel Kent (41 pen) Jordan Fielding (62) Christian Holliday (79) |
| 2020-10-17 15:00:0017/10/20 | Brandon United v Crook Town | 1 - 2 | Division 2 | 2020-21 | Welfare Ground | | 147 |
| Kai Hewitson (35) |
| Daniel Kent 2 (6, 21) |
| 2020-10-21 19:30:5821/10/20 | Crook Town v West Auckland Tuns | 6 - 1 | | 2020-21 | The Sir Tom Cowie Millfield | Durham Challenge CupPreliminary Round | 150 |
| Jamie Tumilty 2 (15, 64), Christian Holliday 3 (26, 31, 86), Dane Eltringham (81) |
| Paul Jordan (34) |
| 2020-10-24 15:00:0024/10/20 | Crook Town v Carlisle City | 1 - 2 | Division 2 | 2020-21 | The Sir Tom Cowie Millfield | | 150 |
| Joe Hillerby (64) |
| Dan Kirkup (11) Keighren Kerr (26), Kerr sent off (81) |
| 2020-10-31 15:00:0031/10/20 | Heaton Stannington v Crook Town | 1 - 1 | Division 2 | 2020-21 | Grounsell Park | | 150 |
| Joe Kerridge (70 pen) |
| Daniel Kent (86) |
