| 1. Round | 03/08/2019 | Forest Green Rovers | - | Oldham Athletic | 1:0 | ||||
| 2. Round | 10/08/2019 | Oldham Athletic | - | Crewe Alexandra | 1:2 | ||||
| 4. Round | 20/08/2019 | Oldham Athletic | - | Exeter City | 0:0 | ||||
| 5. Round | 24/08/2019 | Cambridge United | - | Oldham Athletic | 1:2 | ||||
| 6. Round | 31/08/2019 | Oldham Athletic | - | Colchester United | 0:1 | ||||
| 7. Round | 07/09/2019 | Plymouth Argyle | - | Oldham Athletic | 2:2 |  |
|||
| 8. Round | 14/09/2019 | Oldham Athletic | - | Grimsby Town | 2:2 | ||||
| 9. Round | 17/09/2019 | Scunthorpe United | - | Oldham Athletic | 2:2 | |
 |
||
| 10. Round | 21/09/2019 | Oldham Athletic | - | Morecambe FC | 3:1 | ||||
| 11. Round | 28/09/2019 | Carlisle United | - | Oldham Athletic | 1:0 | ||||
| 26. Round | 04/01/2020 | Cheltenham Town | - | Oldham Athletic | 3:0 | ||||
| 30. Round | 28/01/2020 | Oldham Athletic | - | Mansfield Town | 3:1 | ||||
| 32. Round | 08/02/2020 | Crewe Alexandra | - | Oldham Athletic | 2:1 | ||||
| 33. Round | 11/02/2020 | Exeter City | - | Oldham Athletic | 5:1 | ||||
| 34. Round | 15/02/2020 | Oldham Athletic | - | Forest Green Rovers | 1:1 | ||||
| 37. Round | 07/03/2020 | Crawley Town | - | Oldham Athletic | 3:0 |
France