| 2. Ronde | 12.08.2023 | Leyton Orient | - | Portsmouth FC | 0:4 | ||||
| 3. Ronde | 15.08.2023 | Wycombe Wanderers | - | Leyton Orient | 3:2 |  |
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| 4. Ronde | 19.08.2023 | Blackpool FC | - | Leyton Orient | 0:0 | |
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| 5. Ronde | 26.08.2023 | Leyton Orient | - | Cambridge United | 2:0 | ||||
| 6. Ronde | 02.09.2023 | Leyton Orient | - | Stevenage FC | 0:3 | |
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| 12. Ronde | 07.10.2023 | Leyton Orient | - | Reading FC | 2:1 | ||||
| 13. Ronde | 14.10.2023 | Carlisle United | - | Leyton Orient | 0:1 | |
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| 15. Ronde | 24.10.2023 | Northampton Town | - | Leyton Orient | 2:2 | |
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| 17. Ronde | 11.11.2023 | Leyton Orient | - | Oxford United | 2:3 | ||||
| 11. Ronde | 21.11.2023 | Leyton Orient | - | Lincoln City | 0:1 | ||||
| 19. Ronde | 25.11.2023 | Leyton Orient | - | Wigan Athletic | 1:1 | ||||
| 20. Ronde | 28.11.2023 | Bristol Rovers | - | Leyton Orient | 1:1 | |
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| 28. Ronde | 13.01.2024 | Portsmouth FC | - | Leyton Orient | 0:3 |
Engeland