| 1. Round | 03/08/2019 | Forest Green Rovers | - | Oldham Athletic | 1:0 | ||||
| 2. Round | 10/08/2019 | Oldham Athletic | - | Crewe Alexandra | 1:2 | ||||
| 3. Round | 17/08/2019 | Bradford City | - | Oldham Athletic | 3:0 | ||||
| 4. Round | 20/08/2019 | Oldham Athletic | - | Exeter City | 0:0 | ||||
| 5. Round | 24/08/2019 | Cambridge United | - | Oldham Athletic | 1:2 | ||||
| 26. Round | 04/01/2020 | Cheltenham Town | - | Oldham Athletic | 3:0 | ||||
| 27. Round | 11/01/2020 | Macclesfield Town | - | Oldham Athletic | 1:1 | ||||
| 18. Round | 14/01/2020 | Stevenage FC | - | Oldham Athletic | 0:0 | ||||
| 29. Round | 25/01/2020 | Salford City | - | Oldham Athletic | 1:1 |  |
|||
| 30. Round | 28/01/2020 | Oldham Athletic | - | Mansfield Town | 3:1 |  |
|||
| 31. Round | 01/02/2020 | Oldham Athletic | - | Bradford City | 3:0 | ||||
| 32. Round | 08/02/2020 | Crewe Alexandra | - | Oldham Athletic | 2:1 | |
|||
| 34. Round | 15/02/2020 | Oldham Athletic | - | Forest Green Rovers | 1:1 | |
|||
| 36. Round | 29/02/2020 | Oldham Athletic | - | Newport County | 5:0 | ||||
| 37. Round | 07/03/2020 | Crawley Town | - | Oldham Athletic | 3:0 |
Netherlands