| 8. Round | 16/09/2023 | Peterborough United | - | Leyton Orient | 1:1 | ||||
| 9. Round | 23/09/2023 | Leyton Orient | - | Shrewsbury Town | 1:0 | ||||
| 10. Round | 30/09/2023 | Fleetwood Town | - | Leyton Orient | 1:0 | ||||
| 12. Round | 07/10/2023 | Leyton Orient | - | Reading FC | 2:1 | ||||
| 13. Round | 14/10/2023 | Carlisle United | - | Leyton Orient | 0:1 | ||||
| 14. Round | 21/10/2023 | Leyton Orient | - | Barnsley FC | 1:1 | ||||
| 15. Round | 24/10/2023 | Northampton Town | - | Leyton Orient | 2:2 | ||||
| 16. Round | 28/10/2023 | Burton Albion | - | Leyton Orient | 0:0 | ||||
| 17. Round | 11/11/2023 | Leyton Orient | - | Oxford United | 2:3 | ||||
| 11. Round | 21/11/2023 | Leyton Orient | - | Lincoln City | 0:1 | ||||
| 19. Round | 25/11/2023 | Leyton Orient | - | Wigan Athletic | 1:1 | ||||
| 20. Round | 28/11/2023 | Bristol Rovers | - | Leyton Orient | 1:1 |
Ireland