| 1. Ronde | 05.08.2023 | Charlton Athletic | - | Leyton Orient | 1:0 | ||||
| 2. Ronde | 12.08.2023 | Leyton Orient | - | Portsmouth FC | 0:4 | ||||
| 3. Ronde | 15.08.2023 | Wycombe Wanderers | - | Leyton Orient | 3:2 | ||||
| 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 | |
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| 6. Ronde | 02.09.2023 | Leyton Orient | - | Stevenage FC | 0:3 | ||||
| 7. Ronde | 09.09.2023 | Exeter City | - | Leyton Orient | 1:2 | ||||
| 8. Ronde | 16.09.2023 | Peterborough United | - | Leyton Orient | 1:1 | |
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| 9. Ronde | 23.09.2023 | Leyton Orient | - | Shrewsbury Town | 1:0 | ||||
| 10. Ronde | 30.09.2023 | Fleetwood Town | - | Leyton Orient | 1:0 | ||||
| 12. Ronde | 07.10.2023 | Leyton Orient | - | Reading FC | 2:1 | ||||
| 13. Ronde | 14.10.2023 | Carlisle United | - | Leyton Orient | 0:1 | ||||
| 14. Ronde | 21.10.2023 | Leyton Orient | - | Barnsley FC | 1:1 | ||||
| 15. Ronde | 24.10.2023 | Northampton Town | - | Leyton Orient | 2:2 | ||||
| 16. Ronde | 28.10.2023 | Burton Albion | - | Leyton Orient | 0:0 |
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