1. Round | 03/08/2019 | Leyton Orient | - | Cheltenham Town | 1:0 | ||||
2. Round | 10/08/2019 | Macclesfield Town | - | Leyton Orient | 3:0 | ||||
5. Round | 24/08/2019 | Leyton Orient | - | Crawley Town | 2:3 | ||||
8. Round | 14/09/2019 | Exeter City | - | Leyton Orient | 2:2 | ||||
10. Round | 21/09/2019 | Colchester United | - | Leyton Orient | 2:1 | ||||
13. Round | 12/10/2019 | Leyton Orient | - | Walsall FC | 3:1 | ||||
14. Round | 19/10/2019 | Grimsby Town | - | Leyton Orient | 0:4 | ||||
15. Round | 22/10/2019 | Plymouth Argyle | - | Leyton Orient | 4:0 | ||||
18. Round | 16/11/2019 | Leyton Orient | - | Scunthorpe United | 0:2 | ||||
19. Round | 23/11/2019 | Leyton Orient | - | Forest Green Rovers | 2:4 |