1. Round | 03/08/2019 | Leyton Orient | - | Cheltenham Town | 1:0 | ||||
2. Round | 10/08/2019 | Macclesfield Town | - | Leyton Orient | 3:0 | ||||
3. Round | 17/08/2019 | Leyton Orient | - | Stevenage FC | 0:0 | ||||
4. Round | 20/08/2019 | Mansfield Town | - | Leyton Orient | 2:3 | ||||
5. Round | 24/08/2019 | Leyton Orient | - | Crawley Town | 2:3 | ||||
6. Round | 31/08/2019 | Salford City | - | Leyton Orient | 1:1 | ||||
7. Round | 07/09/2019 | Leyton Orient | - | Swindon Town | 1:3 | ||||
8. Round | 14/09/2019 | Exeter City | - | Leyton Orient | 2:2 | ||||
9. Round | 17/09/2019 | Leyton Orient | - | Crewe Alexandra | 1:2 | ||||
10. Round | 21/09/2019 | Colchester United | - | Leyton Orient | 2:1 | ||||
11. Round | 28/09/2019 | Leyton Orient | - | Port Vale FC | 3:3 | ||||
14. Round | 19/10/2019 | Grimsby Town | - | Leyton Orient | 0:4 | ||||
15. Round | 22/10/2019 | Plymouth Argyle | - | Leyton Orient | 4:0 | ||||
16. Round | 26/10/2019 | Leyton Orient | - | Carlisle United | 1:1 | ||||
18. Round | 16/11/2019 | Leyton Orient | - | Scunthorpe United | 0:2 | ||||
25. Round | 01/01/2020 | Walsall FC | - | Leyton Orient | 1:0 |