| 2. Round | 06/08/2019 | Boreham Wood | - | Wrexham AFC | 2:2 | ||||
| 4. Round | 13/08/2019 | Dagenham & Redbridge | - | Boreham Wood | 0:3 | ||||
| 5. Round | 17/08/2019 | Boreham Wood | - | Sutton United | 0:1 | ||||
| 6. Round | 24/08/2019 | Bromley FC | - | Boreham Wood | 1:0 | ||||
| 7. Round | 26/08/2019 | Boreham Wood | - | Ebbsfleet United | 1:2 | ||||
| 8. Round | 31/08/2019 | Chorley FC | - | Boreham Wood | 1:3 | ||||
| 16. Round | 08/10/2019 | Barrow AFC | - | Boreham Wood | 3:1 | ||||
| 17. Round | 12/10/2019 | Halifax Town | - | Boreham Wood | 0:2 | ||||
| 20. Round | 02/11/2019 | Yeovil Town | - | Boreham Wood | 1:1 | ||||
| 26. Round | 21/12/2019 | Boreham Wood | - | Harrogate Town | 2:1 | ||||
| 29. Round | 01/01/2020 | Boreham Wood | - | Barnet FC | 0:0 |
England