| 3. Jornada | 17.08.2019 | Leyton Orient | - | Stevenage FC | 0:0 | ||||
| 4. Jornada | 20.08.2019 | Mansfield Town | - | Leyton Orient | 2:3 | ||||
| 7. Jornada | 07.09.2019 | Leyton Orient | - | Swindon Town | 1:3 | ||||
| 8. Jornada | 14.09.2019 | Exeter City | - | Leyton Orient | 2:2 | ||||
| 9. Jornada | 17.09.2019 | Leyton Orient | - | Crewe Alexandra | 1:2 | ||||
| 10. Jornada | 21.09.2019 | Colchester United | - | Leyton Orient | 2:1 | ||||
| 11. Jornada | 28.09.2019 | Leyton Orient | - | Port Vale FC | 3:3 | ||||
| 12. Jornada | 05.10.2019 | Northampton Town | - | Leyton Orient | 0:1 |  |
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| 13. Jornada | 12.10.2019 | Leyton Orient | - | Walsall FC | 3:1 |  |
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| 14. Jornada | 19.10.2019 | Grimsby Town | - | Leyton Orient | 0:4 | ||||
| 15. Jornada | 22.10.2019 | Plymouth Argyle | - | Leyton Orient | 4:0 | ||||
| 16. Jornada | 26.10.2019 | Leyton Orient | - | Carlisle United | 1:1 | ||||
| 17. Jornada | 02.11.2019 | Morecambe FC | - | Leyton Orient | 1:0 | ||||
| 20. Jornada | 07.12.2019 | Oldham Athletic | - | Leyton Orient | 1:1 | |
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| 34. Jornada | 15.02.2020 | Cheltenham Town | - | Leyton Orient | 2:1 | ||||
| 37. Jornada | 07.03.2020 | Leyton Orient | - | Cambridge United | 2:1 |
Inglaterra