| 3. Ronde | 17.08.2019 | Leyton Orient | - | Stevenage FC | 0:0 | ||||
| 4. Ronde | 20.08.2019 | Mansfield Town | - | Leyton Orient | 2:3 |  |
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| 5. Ronde | 24.08.2019 | Leyton Orient | - | Crawley Town | 2:3 | |
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| 7. Ronde | 07.09.2019 | Leyton Orient | - | Swindon Town | 1:3 | |
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| 8. Ronde | 14.09.2019 | Exeter City | - | Leyton Orient | 2:2 | ||||
| 9. Ronde | 17.09.2019 | Leyton Orient | - | Crewe Alexandra | 1:2 | ||||
| 12. Ronde | 05.10.2019 | Northampton Town | - | Leyton Orient | 0:1 | |
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| 13. Ronde | 12.10.2019 | Leyton Orient | - | Walsall FC | 3:1 | ||||
| 14. Ronde | 19.10.2019 | Grimsby Town | - | Leyton Orient | 0:4 | ||||
| 15. Ronde | 22.10.2019 | Plymouth Argyle | - | Leyton Orient | 4:0 | ||||
| 16. Ronde | 26.10.2019 | Leyton Orient | - | Carlisle United | 1:1 | ||||
| 17. Ronde | 02.11.2019 | Morecambe FC | - | Leyton Orient | 1:0 | ||||
| 19. Ronde | 23.11.2019 | Leyton Orient | - | Forest Green Rovers | 2:4 |
Noord-Ierland