20. Round | 07/12/2019 | Oldham Athletic | - | Leyton Orient | 1:1 | ||||
22. Round | 21/12/2019 | Cambridge United | - | Leyton Orient | 2:3 | ||||
27. Round | 11/01/2020 | Leyton Orient | - | Grimsby Town | 1:1 | ||||
28. Round | 18/01/2020 | Port Vale FC | - | Leyton Orient | 1:0 | ||||
29. Round | 25/01/2020 | Leyton Orient | - | Newport County | 2:1 | ||||
31. Round | 01/02/2020 | Stevenage FC | - | Leyton Orient | 0:3 |