| 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 | ||||
| 6. Round | 31/08/2019 | Oldham Athletic | - | Colchester United | 0:1 | ||||
| 9. Round | 17/09/2019 | Scunthorpe United | - | Oldham Athletic | 2:2 | ||||
| 11. Round | 28/09/2019 | Carlisle United | - | Oldham Athletic | 1:0 | ||||
| 14. Round | 19/10/2019 | Oldham Athletic | - | Macclesfield Town | 0:1 | ||||
| 15. Round | 22/10/2019 | Oldham Athletic | - | Walsall FC | 2:0 | ||||
| 16. Round | 26/10/2019 | Port Vale FC | - | Oldham Athletic | 0:0 | ||||
| 17. Round | 02/11/2019 | Oldham Athletic | - | Northampton Town | 2:2 | ||||
| 22. Round | 21/12/2019 | Oldham Athletic | - | Crawley Town | 2:1 | ||||
| 23. Round | 26/12/2019 | Morecambe FC | - | Oldham Athletic | 1:2 | ||||
| 24. Round | 29/12/2019 | Oldham Athletic | - | Salford City | 1:4 | ||||
| 26. Round | 04/01/2020 | Cheltenham Town | - | Oldham Athletic | 3:0 |
England
